(6R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid → 7-[2-(2,3-Dihydro-1,4-dithiin-5-yl)-2-methoxyiminoacetamido]-3-methyl-3-cephem-4-carboxylic acid

HRID 1758063Notes

Reaction equation

HRID 1758063 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:26](=[O:27])[N:17]2[C:18]([C:23]([OH:25])=[O:24])=[C:19]([CH3:22])[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:26](=[O:27])[N:17]3[C:18]([C:23]([OH:25])=[O:24])=[C:19]([CH3:22])[CH2:20][S:21][C@H:16]23)=[O:10])[S:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 13475828(6R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 539358522-Methoxyimino-2-(2,3-dihydro-1,4-dithiin-5-yl)acetic acid

Product 1

HCID 1317120097-[2-(2,3-Dihydro-1,4-dithiin-5-yl)-2-methoxyiminoacetamido]-3-methyl-3-cephem-4-carboxylic acid

Procedure

2-(2,3-Dihydro-1,4-dithiin-5-yl)-2-methoxyiminoacetic acid (syn isomer, 1.15 g.) was allowed to react with 7-amino-3-methyl-3-cephem-4-carboxylic acid (1.07 g.) in a similar manner to that of Example 1 to give the captioned compound (0.8 g.), pale yellow powder.

Workup

  1. customto give the captioned compound (0.8 g.), pale yellow powder

Sources & evidence

ORD record
ord-06bd662a31a94d0f921ec6122b7fcea4
Source dataset
uspto-grants-1983_02
Patent number
US04371531

Reaction notes

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