2-Methoxyimino-2-(3-hydroxyphenyl)acetic acid → 7-[2-Methoxyimino-2-(3-hydroxyphenyl)acetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid

HRID 1659670Notes

Reaction equation

HRID 1659670 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[CH:9]=1)[C:5]([OH:7])=O.[NH2:15][CH:16]1[C:37](=[O:38])[N:18]2[C:19]([C:34]([OH:36])=[O:35])=[C:20]([CH2:23][O:24][C:25](=[O:33])[NH:26]C(=O)C(Cl)(Cl)Cl)[CH2:21][S:22][C@H:17]12>>[CH3:1][O:2][N:3]=[C:4]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[CH:9]=1)[C:5]([NH:15][CH:16]1[C:37](=[O:38])[N:18]2[C:19]([C:34]([OH:36])=[O:35])=[C:20]([CH2:23][O:24][C:25](=[O:33])[NH2:26])[CH2:21][S:22][C@H:17]12)=[O:7]

Participants

3

Reactant 2

HCID 543905512-Methoxyimino-2-(3-hydroxyphenyl)acetic acidHCID 679007597-Amino-3-trichloroacetylcarbamoyloxymethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317116097-[2-Methoxyimino-2-(3-hydroxyphenyl)acetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acidYield 19.8%

Procedure

2-Methoxyimino-2-(3-hydroxyphenyl)acetic acid (syn isomer) (1.1 g.) and 7-amino-3-trichloroacetylcarbamoyloxymethyl-3-cephem-4-carboxylic acid (2.35 g.) were reacted and post-treated according to a similar manner to that of Example 3 to give 7-[2-methoxyimino-2-(3-hydroxyphenyl)acetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid (syn isomer) (0.5 g.). This compound is identified with the compound obtained in Example 2 by I.R. and N.M.R. spectra.

Workup

  1. additionpost-treated

Sources & evidence

ORD record
ord-39fdf08a5a33404698ee618c1658b0fb
Source dataset
uspto-grants-1981_12
Patent number
US04304770

Reaction notes

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