Phenol → HCID 88764054, compound

HRID 1278320Notes

Reaction equation

HRID 1278320 reaction equation
[NH2:1][CH:2]1[C:13](=[O:14])[N:4]2[C:5](C(O)=O)=[C:6]([Cl:9])[CH2:7][S:8][C@H:3]12.P(Cl)(Cl)Cl.[C:19]1([OH:25])C=CC=CC=1>CN(C)C=O.O>[CH:19]([NH:1][C@@H:2]1[C:13](=[O:14])[N:4]2[CH:5]=[C:6]([Cl:9])[CH2:7][S:8][C@H:3]12)=[O:25]

Participants

6

Reactant 3

HCID 996PhenolHCID 24387Phosphorus trichlorideHCID 23620956HCID 23620956, compound

Product 1

HCID 88764054HCID 88764054, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

This invention relates to a process for the preparation of 7-amino-3-chloro-3-cephem-4-carboxylic acid and esters thereof and to useful intermediates. In particular, it relates to a process for preparing the 3-chloro nucleus which comprises reacting a 7-amino-3-hydroxy-3-cephem ester with a chlorinating agent, for example phosphorus trichloride, in dimethylformamide to produce a 7β-[(dimethylaminomethylene)amino]-3-chloro-3-cephem ester which, on reaction with a carboxylic acid, a percarboxylic acid, or a phenol having a pH in water of between about 2.0 and about 5, forms the corresponding 7β-formamido-3-chloro ester. The product is obtained as an isomeric mixture of 7β-formamido-3-chloro-3-cephem and the corresponding 2-cephem when the 7-amidino-3-chloro intermediate is reacted with a weakly acidic carboxylic acid or with a phenol.

Sources & evidence

ORD record
ord-8746e2b3d741473e91fdccb229b87d34
Source dataset
uspto-grants-1981_07
Patent number
US04281117

Reaction notes

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