7-Amino-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylicacid → 7-[2-(2,3-Dihydro-1,4-dithiin-5-yl)-2-methoxyiminoacetamido]-3-(1-methyl-1H-tetrazol-5yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 615757Notes

Reaction equation

HRID 615757 reaction equation
[S:1]1[CH:6]=[C:5]([C:7](=[N:11][O:12][CH3:13])[C:8]([OH:10])=O)[S:4][CH2:3][CH2:2]1.[NH2:14][CH:15]1[C:33](=[O:34])[N:17]2[C:18]([C:30]([OH:32])=[O:31])=[C:19]([CH2:22][S:23][C:24]3[N:28]([CH3:29])[N:27]=[N:26][N:25]=3)[CH2:20][S:21][C@H:16]12>>[S:1]1[CH:6]=[C:5]([C:7](=[N:11][O:12][CH3:13])[C:8]([NH:14][CH:15]2[C:33](=[O:34])[N:17]3[C:18]([C:30]([OH:32])=[O:31])=[C:19]([CH2:22][S:23][C:24]4[N:28]([CH3:29])[N:27]=[N:26][N:25]=4)[CH2:20][S:21][C@H:16]23)=[O:10])[S:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 130208137-Amino-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylicacidHCID 539358522-Methoxyimino-2-(2,3-dihydro-1,4-dithiin-5-yl)acetic acid

Product 1

HCID 1317141187-[2-(2,3-Dihydro-1,4-dithiin-5-yl)-2-methoxyiminoacetamido]-3-(1-methyl-1H-tetrazol-5yl)thiomethyl-3-cephem-4-carboxylic acid

Procedure

2-(2,3-Dihydro-1,4-dithiin-5-yl)-2-methoxyiminoacetic acid (syn isomer, 1.2 g.) was allowed to react with 7-amino-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (1.65 g.) in a similar manner to that of Example 1 to give the captioned compound (2.1 g.), pale yellowish white powder.

Workup

  1. customto give the captioned compound (2.1 g.), pale yellowish white powder

Sources & evidence

ORD record
ord-d890dee615294dcc8a1a947b411173c6
Source dataset
uspto-grants-1985_02
Patent number
US04500709

Reaction notes

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