JPS5446741A - Preparation of hydroxy-phenyl glycine derivatives - Google Patents
Preparation of hydroxy-phenyl glycine derivativesInfo
- Publication number
- JPS5446741A JPS5446741A JP11204277A JP11204277A JPS5446741A JP S5446741 A JPS5446741 A JP S5446741A JP 11204277 A JP11204277 A JP 11204277A JP 11204277 A JP11204277 A JP 11204277A JP S5446741 A JPS5446741 A JP S5446741A
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- salt
- glyoxylic acid
- derivatives
- preparation
- 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.)
- Pending
Links
- KKLMJYDGZSAIQX-UHFFFAOYSA-N 2-(n-hydroxyanilino)acetic acid Chemical class OC(=O)CN(O)C1=CC=CC=C1 KKLMJYDGZSAIQX-UHFFFAOYSA-N 0.000 title 1
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 abstract 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 abstract 2
- 150000002989 phenols Chemical class 0.000 abstract 2
- -1 potassium salt Chemical class 0.000 abstract 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 abstract 1
- 239000005695 Ammonium acetate Substances 0.000 abstract 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- 229930186147 Cephalosporin Natural products 0.000 abstract 1
- LJCWONGJFPCTTL-SSDOTTSWSA-N D-4-hydroxyphenylglycine Chemical class [O-]C(=O)[C@H]([NH3+])C1=CC=C(O)C=C1 LJCWONGJFPCTTL-SSDOTTSWSA-N 0.000 abstract 1
- 229930182555 Penicillin Natural products 0.000 abstract 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- 229940043376 ammonium acetate Drugs 0.000 abstract 1
- 235000019257 ammonium acetate Nutrition 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 229940124587 cephalosporin Drugs 0.000 abstract 1
- 150000001780 cephalosporins Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229960001867 guaiacol Drugs 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 229940049954 penicillin Drugs 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
PURPOSE: To obtain the titled compounds useful as raw materials for synthetic penicillin or cephalosporin antibiotics readily in high yield without using conc. aqueous ammonia, by reacting phenol derivatives with glyoxylic acid under suitable conditions in one stage.
CONSTITUTION: Phenol derivatives of formulaI: (ring A is phenyl group having one or two or more groups selected from halogen, carboxyl, lower alkyl, and lower alkoxy groups in the o-or/and m-positions to OH), e.g. guaiacol, o-cresol, etc. are reacted with glyoxylic acid or its salt, e.g. potassium salt, etc. and an ammonium salt, e.g. ammonium acetate, etc. in an aqueous solution or hydrous lower alkanol e.g. hydrous methanol, etc. under neutral or weakly acidic conditions, preferably at 20W40°C to give 4-hydroxy-phenylglycine derivatives of formula II.
COPYRIGHT: (C)1979,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11204277A JPS5446741A (en) | 1977-09-16 | 1977-09-16 | Preparation of hydroxy-phenyl glycine derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11204277A JPS5446741A (en) | 1977-09-16 | 1977-09-16 | Preparation of hydroxy-phenyl glycine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5446741A true JPS5446741A (en) | 1979-04-12 |
Family
ID=14576551
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11204277A Pending JPS5446741A (en) | 1977-09-16 | 1977-09-16 | Preparation of hydroxy-phenyl glycine derivatives |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5446741A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5336805A (en) * | 1991-08-13 | 1994-08-09 | Dsm N.V. | Process for preparing an α-amino acid, the corresponding ester and amide |
-
1977
- 1977-09-16 JP JP11204277A patent/JPS5446741A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5336805A (en) * | 1991-08-13 | 1994-08-09 | Dsm N.V. | Process for preparing an α-amino acid, the corresponding ester and amide |
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