FR2338249A1 - Alpha aromatic N-acyl glycine intermediates for penicillins - prepd. from an amido glycollic acid and an aromatic cpd. - Google Patents
Alpha aromatic N-acyl glycine intermediates for penicillins - prepd. from an amido glycollic acid and an aromatic cpd.Info
- Publication number
- FR2338249A1 FR2338249A1 FR7601178A FR7601178A FR2338249A1 FR 2338249 A1 FR2338249 A1 FR 2338249A1 FR 7601178 A FR7601178 A FR 7601178A FR 7601178 A FR7601178 A FR 7601178A FR 2338249 A1 FR2338249 A1 FR 2338249A1
- Authority
- FR
- France
- Prior art keywords
- aromatic
- acid
- prepd
- substd
- penicillins
- 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.)
- Granted
Links
- 125000003118 aryl group Chemical group 0.000 title abstract 4
- 229930182555 Penicillin Natural products 0.000 title abstract 2
- 239000000543 intermediate Substances 0.000 title abstract 2
- 150000002960 penicillins Chemical class 0.000 title abstract 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 title 1
- 239000004471 Glycine Substances 0.000 title 1
- -1 amido glycollic acid Chemical compound 0.000 title 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- UYEMGAFJOZZIFP-UHFFFAOYSA-N 3,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC(O)=C1 UYEMGAFJOZZIFP-UHFFFAOYSA-N 0.000 abstract 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 abstract 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 2
- 229930192474 thiophene Natural products 0.000 abstract 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 abstract 1
- 229940076286 cupric acetate Drugs 0.000 abstract 1
- 150000002333 glycines Chemical class 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The substd. N-acylated glycines Ar-CH(COOH)-NHCOR (I) are prepd. by the reaction of a carboxamide glycolic acid HOCH(COOH)-NHCOR (II) with an aromatic cpd. ArH (III), the reaction being effected in the presence of a strong mineral acid and a minimum of water (where Ar is an aromatic group which may be substd. and may have >=1 rings; R is (un)satd. alkyl, which may be substd). The prods are intermediates for the prepn. of semisynthetic penicillins. The process is general in its application, is simple to carry out, and gives good yields. Typically (III) is thiophene, benzene, phenol or 3,5-dihydroxy benzoic acid and R is methyl. In an example, 36.8g thiophene was treated with 65.2g (II hydrate, R-CO = acryloyl) in acetic acid/sulphyric acid contg. cupric acetate to give 50% yield of N-acryloyl thienylglycine, mpt. 140 degrees C.
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7601178A FR2338249A1 (en) | 1976-01-16 | 1976-01-16 | Alpha aromatic N-acyl glycine intermediates for penicillins - prepd. from an amido glycollic acid and an aromatic cpd. |
| BE168798A BE843994A (en) | 1975-09-12 | 1976-07-09 | PROCESS FOR MANUFACTURING N-ACYL DERIVATIVES OF GLYCINES & -SUBSTITUTED BY AROMATIC RADICALS AND NEW PRODUCTS RESULTING |
| IT5093476A IT1066142B (en) | 1975-09-12 | 1976-08-18 | Alpha aromatic N-acyl glycine intermediates for penicillins - prepd. from an amido glycollic acid and an aromatic cpd. |
| NL7609939A NL7609939A (en) | 1975-09-12 | 1976-09-08 | PROCESS FOR THE PREPARATION OF N-ACYLHYDROXYARYL GLYCINS. |
| CH1141676A CH614928A5 (en) | 1975-09-12 | 1976-09-08 | |
| CA260,800A CA1066304A (en) | 1975-09-12 | 1976-09-08 | Process for manufacturing n-acyl derivatives of hydroxyarylgycines and novel products resulting therefrom |
| DE19762640615 DE2640615A1 (en) | 1975-09-12 | 1976-09-09 | PROCESS FOR THE PREPARATION OF N-ACYLATED HYDROXYARYLGLYCINE DERIVATIVES AND THE PRODUCTS OBTAINED THEREOF |
| JP51108725A JPS5236644A (en) | 1975-09-12 | 1976-09-09 | Production of nnacyl derivatives of hydroxy arylglycine |
| US05/722,284 US4105690A (en) | 1975-09-12 | 1976-09-10 | Process for manufacturing N-acyl derivatives of hydroxy-arylglycines |
| SE7610064A SE7610064L (en) | 1975-09-12 | 1976-09-10 | METHOD OF PREPARATION OF N-ACYLATED DERIVATIVES OF HYDROXYARYLGLYCINES |
| GB37651/76A GB1520824A (en) | 1975-09-12 | 1976-09-10 | Process for manufacturing n-acyl derivatives of hydroxy-arylglycines |
| SE7610065A SE7610065L (en) | 1975-09-12 | 1976-09-10 | METHOD OF PREPARATION N-ACYLATED DERIVATIVES OF GLYCINS SUBSTITUTED WITH AROMATIC RADICALS |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7601178A FR2338249A1 (en) | 1976-01-16 | 1976-01-16 | Alpha aromatic N-acyl glycine intermediates for penicillins - prepd. from an amido glycollic acid and an aromatic cpd. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2338249A1 true FR2338249A1 (en) | 1977-08-12 |
| FR2338249B1 FR2338249B1 (en) | 1980-11-14 |
Family
ID=9168047
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7601178A Granted FR2338249A1 (en) | 1975-09-12 | 1976-01-16 | Alpha aromatic N-acyl glycine intermediates for penicillins - prepd. from an amido glycollic acid and an aromatic cpd. |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2338249A1 (en) |
-
1976
- 1976-01-16 FR FR7601178A patent/FR2338249A1/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2338249B1 (en) | 1980-11-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CD | Change of name or company name | ||
| TP | Transmission of property | ||
| ST | Notification of lapse |