CN119219602A - A 4-lauryl-β-lactam derivative and preparation method thereof - Google Patents
A 4-lauryl-β-lactam derivative and preparation method thereof Download PDFInfo
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Abstract
本发明公开了一种4‑月桂基‑β‑内酰胺衍生物及其制备方法，所述4‑月桂基‑β‑内酰胺衍生物的结构式如下所示：其中，R1、R2独立选自氢、C1‑C6饱和或不饱和烷基、取代或未取代苯甲基中的一种。可以利于简单的原料一步构建高收率的4‑月桂基‑β‑内酰胺衍生物，反应条件温和，后处理过程简单，适合规模化生产。The present invention discloses a 4-lauryl-β-lactam derivative and a preparation method thereof. The structural formula of the 4-lauryl-β-lactam derivative is as follows: Wherein, R 1 and R 2 are independently selected from one of hydrogen, C1-C6 saturated or unsaturated alkyl, substituted or unsubstituted benzyl. It is convenient to construct a high-yield 4-lauryl-β-lactam derivative in one step with simple raw materials, with mild reaction conditions and simple post-treatment process, and is suitable for large-scale production.
Description
Technical Field
The invention relates to the field of organic synthesis, in particular to a 4-lauryl-beta-lactam derivative and a preparation method thereof.
Background
Beta-lactam is an important component in N heterocycle, and some natural products and drug molecules have the core skeleton, and especially the single-ring quaternary nitrogen-containing heterocycle antibiotics used for clinic have become special drugs for treating diseases such as pancreatitis and the like.
The synthesis methods of the beta-lactam derivatives to date mainly comprise (1) preparing the beta-lactam derivatives by means of reduction cyclization reaction (J.org.chem.1995, 60,1276), (2) synthesizing the beta-lactam (ANGEWANDTE CHEMIE 2014,53,3496) by means of C-H bond activation and metal catalysis, (3) synthesizing the beta-lactam by means of free radical-promoted addition cyclization reaction (chem.common.2019, 55,10523), and (4) synthesizing the beta-lactam by means of free radical series-connected unactivated double bond carboamination reaction (J.am.chem.Soc.2021, 143, 1195-1202), but the free radicals introduced in the molecules are generally of special structures, high-efficiency coupling of large-volume linear hydrocarbon groups cannot be realized, and the preparation and addition of additional oxidants and the generation of free radical donor byproducts are not in accordance with the requirements of high efficiency, atom economy and environmental friendliness. Based on this, a need exists for a method that can efficiently construct different β -lactam derivatives.
Disclosure of Invention
The technical problem to be solved by the invention is to provide the 4-lauryl-beta-lactam derivative and the preparation method thereof, wherein the 4-lauryl-beta-lactam derivative can be efficiently synthesized by initiating the serial cyclization reaction of the lauroyl peroxide, and the preparation method has the advantages of simple preparation process, mild reaction condition, high atomic utilization rate and good universality, accords with green chemistry, and is suitable for large-scale production.
To solve the above technical problem, a first aspect of the present invention provides a 4-lauryl- β -lactam derivative, wherein the structural formula of the 4-lauryl- β -lactam derivative is shown in IV:
Wherein R 1、R2 is independently selected from one of hydrogen, C1-C6 saturated or unsaturated alkyl and substituted or unsubstituted benzyl.
Further, R 1、R2 is independently selected from hydrogen, methyl, ethyl, allyl, cyclopropylmethyl, benzyl, or p-methylbenzyl.
Further, the 4-lauryl- β -lactam derivative is selected from the structures represented by formulas IV-1 to IV-8:
in a second aspect, the present invention provides a process for the preparation of a 4-lauryl- β -lactam derivative according to the first aspect, comprising:
reacting a compound shown in a formula (I) with a compound shown in a formula (II) in the presence of a metal salt catalyst and a solvent to obtain the 4-lauryl-beta-lactam derivative;
The structures of the compound represented by the above formula (I) and the compound represented by the formula (II) are as follows:
Wherein R 1、R2 is independently selected from one of hydrogen, C1-C6 saturated or unsaturated alkyl and substituted or unsubstituted benzyl.
Further, the compound shown in the formula (I) is selected from one of N- (5-iodoquinolin-8-yl) -3-butenamide, N- (5-iodoquinolin-8-yl) -2-methyl-3-butenamide, 2-ethyl-N- (5-iodoquinolin-8-yl) -3-butenamide, N- (5-iodoquinolin-8-yl) -2, 2-dimethyl-3-butenamide, N- (5-iodoquinolin-8-yl) -2-vinyl-4-pentenamide, 2- (cyclopropylmethyl) -N- (5-iodoquinolin-8-yl) -3-butenamide, 2-benzyl-N- (5-iodoquinolin-8-yl) -3-butenamide, N- (5-iodoquinolin-8-yl) -2- (4-methylbenzyl) -3-butenamide, and the structural formulas are respectively shown as follows:
Further, the metal salt catalyst is selected from one or more of cuprous bromide, cuprous iodide, cupric acetate, cuprous chloride, cupric tetraacetonitrile hexafluorophosphate and cuprous trifluoromethane sulfonate.
Preferably, the metal catalyst is selected from one or more of cuprous iodide, copper tetraacetonitrile hexafluorophosphate, and cuprous trifluoromethane sulfonate.
Further, the solvent is selected from one or more of acetonitrile, toluene, methylene dichloride, 1, 2-dichloroethane, 1, 4-dioxane, methyl tertiary butyl ether and tetrahydrofuran.
Further, the molar ratio of the compound shown in the formula (I), the compound shown in the formula (II), the metal salt catalyst and the solvent is 1:1-3:0.02-0.7, preferably 1:1-3:0.05-0.2, and for example, the molar ratio of the compound shown in the formula (I), the compound shown in the formula (II) and the metal salt catalyst is 1:2:0.2, 1:2:0.02, 1:2:0.7, and 1:2:0.1.
Further, the ratio of the molar amount of the compound represented by the formula (I) to the volume of the solvent is 1mmol (5-30) mL, for example, 1mmol:5mL, 1mmol:10mL, 1mmol:15mL, 1mmol:20mL, 1mmol:25mL, 1mmol:30mL, etc.
Further, the temperature of the reaction is 60-100 ℃, e.g., 60 ℃,70 ℃, 80 ℃, 90 ℃, 100 ℃, etc., including but not limited to the temperatures listed above.
The invention has the beneficial effects that:
1. The invention provides a method for preparing the 4-lauryl-beta-lactam derivative, which takes substituted N- (5-iodoquinoline-3-butenamide derivative and lauroyl peroxide as reactants, utilizes double bond free radical addition reaction promoted by lauroyl free radical to efficiently synthesize the 4-lauryl-beta-lactam derivative, has the advantages of easily available raw materials, high atom utilization rate, good universality and environmental protection, and is suitable for batch preparation of the beta-lactam derivative
2. According to the 4-lauryl-beta-lactam derivative provided by the invention, the lipid solubility of molecules can be increased by introducing a large volume of linear alkyl into beta-lactam molecules, so that the diffusion of the small molecule drug in vivo is facilitated, and the concentration of active substances reaching target positions is increased.
Detailed Description
The present invention will be further described with reference to specific examples, which are not intended to be limiting, so that those skilled in the art will better understand the present invention and practice it.
EXAMPLE 1 Synthesis of a Compound of formula IV-1
N- (5-iodoquinolin-8-yl) -3-butenamide (0.068 g,0.20mmol of the compound represented by formula (1)) was weighed, cuOTf (0.04 g,0.04 mmol) was dissolved in 2mL of tetrahydrofuran, and lauroyl peroxide (0.1592 g,0.40 mmol) was added. The mixture was heated to 80 ℃ for reaction, TLC followed the reaction until the reaction was complete. After the reaction, the crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate=20:1) to obtain the product IV-1, the isolation yield was 49%.
The nuclear magnetic characterization of IV-1 is carried out, and the result is:
1H NMR(400MHz,Chloroform-d)δ8.80(dd,J＝4.1,1.7Hz,1H),8.35(dd,J＝8.6,1.6Hz,1H),8.05(s,2H),7.47(dd,J＝8.6,4.1Hz,1H),5.14(ddt,J＝8.8,5.7,3.0Hz,1H),3.31(dd,J＝15.1,5.4Hz,1H),2.80(dd,J＝15.1,2.6Hz,1H),1.95(dddd,J＝12.8,9.3,6.3,3.3Hz,1H),1.47(ddd,J＝14.6,11.2,6.9Hz,1H),1.22(d,J＝14.0Hz,20H),0.87(t,J＝6.8Hz,3H).
13C NMR(101MHz,Chloroform-d)δ166.74,149.41,140.41,137.71,134.88,122.91,122.49,91.95,56.80,43.23,33.62,31.92,29.65,29.62,29.49,29.42,29.35,29.33,24.97,22.70,14.14.
EXAMPLE 2 Synthesis of Compound of formula IV-1
N- (5-iodoquinolin-8-yl) -3-butenamide (0.068 g,0.20mmol of the compound represented by formula (1)) was weighed, cuOTf (0.04 g,0.04 mmol) was dissolved in 2mL of tetrahydrofuran, and lauroyl peroxide (0.1592 g,0.40 mmol) was added. The mixture was heated to 60 ℃ for reaction, TLC followed the reaction until the reaction was complete. After the reaction, the crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate=20:1) to obtain the product IV-1, the isolation yield was 36%.
EXAMPLE 3 Synthesis of Compound of formula IV-1
N- (5-iodoquinolin-8-yl) -3-butenamide (0.068 g,0.20mmol of the compound represented by formula (1)) was weighed, cuOTf (0.04 g,0.04 mmol) was dissolved in 2mL of tetrahydrofuran, and lauroyl peroxide (0.1592 g,0.40 mmol) was added. The mixture was heated to 100 ℃ for reaction, TLC followed the reaction until the reaction was complete. After the reaction, the crude product is purified by silica gel column chromatography (petroleum ether: ethyl acetate=20:1) to obtain the product IV-1, wherein the separation yield is 45%.
EXAMPLE 4 Synthesis of Compound of formula IV-1
N- (5-iodoquinolin-8-yl) -3-butenamide (compound 0.068g,0.20 mmol) represented by formula (1) was weighed, cu (CH 3CN)4PF6 (0.015 g,0.04 mmol) was dissolved in 2mL of tetrahydrofuran, lauroyl peroxide (0.1592 g,0.40 mmol) was added, the mixture was heated to 100 ℃ for reaction, TLC was followed until the reaction was completed, and after completion of the reaction, the crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate=20:1) to give product IV-1 in a separation yield of 15%.
EXAMPLE 5 Synthesis of Compound of formula IV-1
N- (5-iodoquinolin-8-yl) -3-butenamide (0.068 g,0.20mmol of the compound represented by formula (1)) was weighed, cuOTf (0.014 g,0.14 mmol) was dissolved in 2mL of tetrahydrofuran, and lauroyl peroxide (0.1592 g,0.40 mmol) was added. The mixture was heated to 80 ℃ for reaction, TLC followed the reaction until the reaction was complete. After the reaction, the crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate=20:1) to obtain the product IV-1, the isolation yield was 39%.
EXAMPLE 6 Synthesis of Compound of formula IV-1
N- (5-iodoquinolin-8-yl) -3-butenamide (0.068 g,0.20mmol of the compound represented by formula (1)) was weighed out, cuI (0.04 g,0.02 mmol) was dissolved in 2mL of tetrahydrofuran, and lauroyl peroxide (0.1592 g,0.40 mmol) was added. The mixture was heated to 80 ℃ for reaction, TLC followed the reaction until the reaction was complete. After the reaction, the crude product is purified by silica gel column chromatography (petroleum ether: ethyl acetate=20:1) to obtain the product IV-1, wherein the separation yield is 10%.
EXAMPLE 7 Synthesis of Compound of formula IV-2
N- (5-iodoquinolin-8-yl) -2-methyl-3-butenamide (0.070 g,0.20 mmol) of the compound represented by formula (2) was weighed, cuOTf (0.04 g,0.04 mmol) was dissolved in 2mL of tetrahydrofuran, and lauroyl peroxide (0.1592 g,0.40 mmol) was added. The mixture was heated to 80 ℃ for reaction, TLC followed the reaction until the reaction was complete. After the reaction, the crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate=20:1) to obtain compound IV-2, with a separation yield of 43%.
The nuclear magnetic characterization of IV-2 is carried out, and the result is:
1H NMR(400MHz,Chloroform-d)δ8.80(dd,J＝4.1,1.7Hz,1H),8.35(dd,J＝8.6,1.6Hz,1H),8.05(s,2H),7.47(dd,J＝8.6,4.1Hz,1H),4.75(dt,J＝9.4,2.8Hz,1H),3.00(qd,J＝7.3,2.4Hz,1H),1.96(dddd,J＝12.2,8.9,5.8,3.1Hz,1H),1.48(d,J＝7.4Hz,4H),1.23(d,J＝9.2Hz,20H),0.87(t,J＝6.8Hz,3H).
13C NMR(101MHz,Chloroform-d)δ170.24,149.34,140.36,137.70,134.82,122.85,122.65,65.22,51.11,33.35,31.92,29.66,29.63,29.50,29.42,29.41,29.35,25.20,22.70,14.13,13.81.
EXAMPLE 8 Synthesis of Compound of formula IV-3
2-Ethyl-N- (5-iodoquinolin-8-yl) -3-butenamide (0.073 g,0.20mmol of the compound represented by formula (3)) was weighed, cuOTf (0.04 g,0.04 mmol) was dissolved in 2mL of tetrahydrofuran, and lauroyl peroxide (0.1592 g,0.40 mmol) was added. The mixture was heated to 80 ℃ for reaction, TLC followed the reaction until the reaction was complete. After the reaction, the crude product is purified by silica gel column chromatography (petroleum ether: ethyl acetate=20:1) to obtain the compound IV-3, wherein the separation efficiency is 39%.
The nuclear magnetic characterization of IV-3 is carried out, and the result is:
1H NMR(400MHz,Chloroform-d)δ8.80(dd,J＝4.1,1.6Hz,1H),8.34(dd,J＝8.6,1.6Hz,1H),8.06(q,J＝8.2Hz,2H),7.46(dd,J＝8.6,4.1Hz,1H),4.83(dt,J＝9.3,2.8Hz,1H),2.92(ddd,J＝8.4,5.9,2.3Hz,1H),2.05–1.80(m,3H),1.55–1.41(m,1H),1.34–1.17(m,20H),1.12(t,J＝7.4Hz,3H),0.87(t,J＝6.8Hz,3H).
13C NMR(101MHz,Chloroform-d)δ169.77,149.32,140.34,137.71,134.85,130.50,122.83,122.55,91.66,63.23,58.00,33.41,31.92,29.65,29.63,29.50,29.45,29.41,29.35,25.25,22.70,22.28,14.14,11.94.
EXAMPLE 9 Synthesis of Compound of formula IV-4
N- (5-iodoquinolin-8-yl) -2, 2-dimethyl-3-butenamide (0.073 g,0.20mmol of the compound represented by formula (4)) was weighed, cuOTf (0.04 g,0.04 mmol) was dissolved in 2mL of tetrahydrofuran, and lauroyl peroxide (0.159 g,0.40 mmol) was added. The mixture was heated to 80 ℃ for reaction, TLC followed the reaction until the reaction was complete. After the reaction, the crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate=20:1) to obtain compound IV-4, with a separation yield of 56%.
The nuclear magnetic characterization of IV-4 is carried out, and the result is:
1H NMR(400MHz,Chloroform-d)δ8.80(dd,J＝4.2,1.7Hz,1H),8.33(dd,J＝8.6,1.6Hz,1H),8.10–7.91(m,2H),7.46(dd,J＝8.6,4.1Hz,1H),4.82(dd,J＝10.0,3.6Hz,1H),1.84–1.74(m,1H),1.57–1.47(m,4H),1.34(s,3H),1.22(d,J＝12.0Hz,20H),0.87(t,J＝6.8Hz,3H).
13C NMR(101MHz,Chloroform-d)δ173.45,149.41,140.34,137.64,134.58,130.53,123.53,122.85,68.54,53.17,31.92,29.74,29.67,29.64,29.62,29.59,29.51,29.39,29.35,26.15,23.65,22.70,16.96,14.15.
EXAMPLE 10 Synthesis of Compound of formula IV-5
N- (5-iodoquinolin-8-yl) -2-vinyl-4-pentenamide (0.076 g,0.20 mmol) of the compound represented by formula (5) was weighed out, cuOTf (0.04 g,0.04 mmol) was dissolved in 2mL of tetrahydrofuran, and lauroyl peroxide (0.1592 g,0.40 mmol) was added. The mixture was heated to 80 ℃ for reaction, TLC followed the reaction until the reaction was complete. After the reaction, the crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate=20:1) to obtain compound IV-5, with a separation yield of 56%.
The nuclear magnetic characterization of IV-5 is carried out, and the result is:
1H NMR(400MHz,Chloroform-d)δ8.80(dd,J＝4.1,1.7Hz,1H),8.34(dd,J＝8.6,1.6Hz,1H),8.16–7.98(m,2H),7.46(dd,J＝8.6,4.1Hz,1H),5.92(ddt,J＝17.0,10.1,7.0Hz,1H),5.31–5.07(m,2H),4.86(dt,J＝9.3,2.9Hz,1H),3.04(ddd,J＝9.1,5.5,2.3Hz,1H),2.78–2.50(m,2H),1.93(dddd,J＝12.9,9.4,6.3,3.3Hz,1H),1.48(dtd,J＝13.9,9.2,4.8Hz,1H),1.22(d,J＝14.9Hz,20H),0.87(t,J＝6.8Hz,3H).
13C NMR(101MHz,Chloroform-d)δ169.00,149.38,140.35,137.69,134.93,122.86,122.57,117.26,91.82,63.11,55.88,33.41,33.26,31.92,29.66,29.63,29.51,29.39,29.35,25.17,22.70,14.14.
EXAMPLE 11 Synthesis of Compound of formula IV-6
2- (Cyclopropylmethyl) -N- (5-iodoquinolin-8-yl) -3-butenamide (0.078 g,0.20mmol of the compound represented by formula (6)) was weighed out, cuOTf (0.04 g,0.04 mmol) was dissolved in 2mL of tetrahydrofuran, and lauroyl peroxide (0.159 g,0.40 mmol) was added. The mixture was heated to 80 ℃ for reaction, TLC followed the reaction until the reaction was complete. After the reaction, the crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate=20:1) to obtain compound IV-6, the isolation yield was 30%.
The nuclear magnetic characterization of IV-6 is carried out, and the result is:
1H NMR(400MHz,Chloroform-d)δ8.80(dd,J＝4.1,1.7Hz,1H),8.34(dd,J＝8.6,1.6Hz,1H),8.06(q,J＝8.2Hz,2H),7.47(dd,J＝8.6,4.1Hz,1H),4.92(dt,J＝9.3,2.9Hz,1H),3.07(ddd,J＝8.5,6.4,2.3Hz,1H),1.96(dddd,J＝12.2,8.9,6.3,3.0Hz,1H),1.82–1.74(m,2H),1.54–1.44(m,1H),1.39–1.17(m,20H),0.95–0.82(m,4H),0.60–0.45(m,2H),0.26–0.09(m,2H).
13C NMR(101MHz,Chloroform-d)δ169.72,149.33,140.34,137.71,130.50,122.83,122.55,63.48,56.95,34.07,33.55,31.92,29.66,29.63,29.51,29.48,29.44,29.35,25.25,22.70,14.13,9.27,5.14,4.49.
EXAMPLE 12 Synthesis of Compound of formula IV-7
2-Benzyl-N- (5-iodoquinolin-8-yl) -3-butenamide (0.086 g,0.20mmol of the compound represented by formula (7)) was weighed, cuOTf (0.04 g,0.04 mmol) was dissolved in 2mL of tetrahydrofuran, and lauroyl peroxide (0.159 g,0.40 mmol) was added. The mixture was heated to 80 ℃ for reaction, TLC followed the reaction until the reaction was complete. After the reaction, the crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate=20:1) to obtain compound IV-7, with a separation yield of 52%.
The nuclear magnetic characterization of IV-7 is carried out, and the result is:
1H NMR(400MHz,Chloroform-d)δ8.79(dd,J＝4.1,1.6Hz,1H),8.34(dd,J＝8.6,1.6Hz,1H),8.13–8.00(m,2H),7.46(dd,J＝8.6,4.1Hz,1H),7.33(d,J＝4.4Hz,4H),7.26–7.21(m,1H),4.90(dt,J＝9.5,2.8Hz,1H),3.36(dd,J＝13.8,5.0Hz,1H),3.22(ddd,J＝10.1,5.0,2.3Hz,1H),3.02(dd,J＝13.8,10.2Hz,1H),1.81(dddd,J＝13.0,9.7,6.6,3.2Hz,1H),1.43–0.95(m,20H),0.88(t,J＝6.9Hz,4H).
13C NMR(101MHz,Chloroform-d)δ168.97,149.40,140.35,139.14,137.69,134.72,130.51,128.94,128.61,126.56,122.88,122.66,91.95,63.50,58.29,35.39,33.28,31.94,29.67,29.65,29.62,29.37,29.32,29.24,24.75,22.72,14.15.
EXAMPLE 13 Synthesis of Compound of formula IV-8
N- (5-iodoquinolin-8-yl) -2- (4-methylbenzyl) -3-butenamide (0.088 g,0.20mmol of the compound represented by formula (8)) was weighed, cuOTf (0.04 g,0.04 mmol) was dissolved in 2mL of tetrahydrofuran, and lauroyl peroxide (0.159 g,0.40 mmol) was added. The mixture was heated to 80 ℃ for reaction, TLC followed the reaction until the reaction was complete. After the reaction, the crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate=20:1) to obtain compound IV-8, the isolation yield was 51%.
The nuclear magnetic characterization of IV-8 is carried out, and the result is:
1H NMR(400MHz,Chloroform-d)δ8.89–8.70(m,1H),8.42–8.25(m,1H),8.18–7.97(m,2H),7.46(dd,J＝8.4,4.0Hz,1H),7.27–7.10(m,4H),4.89(dt,J＝9.3,2.8Hz,1H),3.32(dd,J＝13.8,4.9Hz,1H),3.26–3.12(m,1H),2.98(dd,J＝13.6,9.9Hz,1H),2.33(s,3H),1.81(dtd,J＝12.8,8.0,6.5,3.3Hz,1H),1.45–0.91(m,21H),0.88(d,J＝7.2Hz,3H).
13C NMR(101MHz,Chloroform-d)δ169.08,149.37,140.33,137.69,136.02,134.79,130.50,129.26,128.80,122.86,122.62,63.51,58.38,34.96,33.31,31.94,29.68,29.40,29.37,29.26,24.78,22.72,21.07,14.16.
The above-described embodiments are merely preferred embodiments for fully explaining the present invention, and the scope of the present invention is not limited thereto. Equivalent substitutions and modifications will occur to those skilled in the art based on the present invention, and are intended to be within the scope of the present invention. The protection scope of the invention is subject to the claims.
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