7-Amino-3-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid → 7-Aminocephalosporanic acid

HRID 426975Notes

Reaction equation

HRID 426975 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7]([CH2:9][C:10]([OH:12])=[O:11])=[O:8].[NH2:13][CH:14]1[C:32](=[O:33])[N:16]2[C:17]([C:29]([OH:31])=[O:30])=[C:18]([CH2:21][S:22][C:23]3[S:27][C:26]([CH3:28])=[N:25][N:24]=3)[CH2:19][S:20][C@H:15]12>>[CH3:9][C:10]([O:12][CH2:21][C:18]1[CH2:19][S:20][C@@H:15]2[C@H:14]([NH2:13])[C:32](=[O:33])[N:16]2[C:17]=1[C:29]([OH:31])=[O:30])=[O:11].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7]([CH2:9][C:10]([NH:13][CH:14]1[C:32](=[O:33])[N:16]2[C:17]([C:29]([OH:31])=[O:30])=[C:18]([CH2:21][S:22][C:23]3[S:27][C:26]([CH3:28])=[N:25][N:24]=3)[CH2:19][S:20][C@H:15]12)=[O:12])=[O:8]

Participants

4

Reactant 2

HCID 129420347-Amino-3-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acidHCID 202971992-Pyridylsulfinylacetic acid

Product 2

HCID 4413287-Aminocephalosporanic acidHCID 1317116487-(2-Pyridylsulfinylacetamido)-3-(2-methyl-1,3,4-thiadiazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid

Procedure

Procedures of Example 10 were repeated by using 2-pyridylsulfinylacetic acid and 7-amino-3-(2-methyl-1,3,4-thiadiazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid instead of the 4-pyridylsulfinylacetic acid and the 7-aminocephalosporanic acid respectively to obtain 7-(2-pyridylsulfinylacetamido)-3-(2-methyl-1,3,4-thiadiazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid of the R form.

Sources & evidence

ORD record
ord-531c6074c9d1415fa30f9eab410931fe
Source dataset
uspto-grants-1979_10
Patent number
US04172197

Reaction notes

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