GB591381A - Manufacture of ª‡-amino-ª‰-thiol-carboxylic esters - Google Patents
Manufacture of ª‡-amino-ª‰-thiol-carboxylic estersInfo
- Publication number
- GB591381A GB591381A GB1153845A GB1153845A GB591381A GB 591381 A GB591381 A GB 591381A GB 1153845 A GB1153845 A GB 1153845A GB 1153845 A GB1153845 A GB 1153845A GB 591381 A GB591381 A GB 591381A
- Authority
- GB
- United Kingdom
- Prior art keywords
- thiol
- methyl
- manufacture
- formylamino
- esterified
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- 235000019441 ethanol Nutrition 0.000 abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 2
- JTGVRUVUKGUTRL-VKHMYHEASA-N (2R)-2-formamido-3-sulfanylpropanoic acid Chemical compound OC(=O)[C@H](CS)NC=O JTGVRUVUKGUTRL-VKHMYHEASA-N 0.000 abstract 1
- CZDHUFYOXKHLME-DFWYDOINSA-N (2S)-2-amino-3-methyl-3-sulfanylbutanoic acid;hydrochloride Chemical compound Cl.CC(C)(S)[C@@H](N)C(O)=O CZDHUFYOXKHLME-DFWYDOINSA-N 0.000 abstract 1
- ORWKVZNEPHTCQE-UHFFFAOYSA-N Acetic formic anhydride Chemical compound CC(=O)OC=O ORWKVZNEPHTCQE-UHFFFAOYSA-N 0.000 abstract 1
- VGGRCVDNFAQIKO-UHFFFAOYSA-N Formic anhydride Chemical compound O=COC=O VGGRCVDNFAQIKO-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M Sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 abstract 1
- 239000004280 Sodium formate Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000002246 antineoplastic agent Substances 0.000 abstract 1
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000005909 ethyl alcohol group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 229960001639 penicillamine Drugs 0.000 abstract 1
- 235000019254 sodium formate Nutrition 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Esters of the formula:-RR1.C.(SH)-CH(NH2).COOR11 in which R and R1 each represent hydrogen or a hydrocarbon radical and R11 represents a hydrocarbon radical are obtained by reacting an a - formylamino - b - thiol - carboxylic acid of the formula: RR1C(SH)-CH(NH.CO.H)-COOH with an alcohol R11OH in the presence of an acid esterification catalyst, e.g. hydrogen chloride. In examples a -formylamino-b -thiol-b -methyl-n-butyric acids are esterified with methyl, benzyl, and ethyl alcohols and N-formylcysteine is esterified with methyl alcohol. The products are useful as intermediates in the manufacture of chemotherapeutic agents. N-formyl penicillamine is obtained by heating together penicillamine hydrochloride, sodium formate, formic acid and acetic anhydride.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB591381A true GB591381A (en) | 1947-08-15 |
Family
ID=1709794
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1153845A Expired GB591381A (en) | 1945-05-07 | Manufacture of ª‡-amino-ª‰-thiol-carboxylic esters |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB591381A (en) |
-
1945
- 1945-05-07 GB GB1153845A patent/GB591381A/en not_active Expired
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