7-Aminodeacetoxycephalosporanic acid → 7-Cyanomethylsulfonylacetamido-3-methyl-3-cephem-4-carboxylic acid

HRID 1658195Notes

Reaction equation

[CH3:1][C:2]1[CH2:11][S:10][C@@H:5]2[C@H:6]([NH2:9])[C:7](=[O:8])[N:4]2[C:3]=1[C:12]([OH:14])=[O:13].[C:15]([CH2:17][S:18]([CH2:21][C:22](O)=[O:23])(=[O:20])=[O:19])#[N:16]>>[C:15]([CH2:17][S:18]([CH2:21][C:22]([NH:9][CH:6]1[C:7](=[O:8])[N:4]2[C:3]([C:12]([OH:14])=[O:13])=[C:2]([CH3:1])[CH2:11][S:10][C@H:5]12)=[O:23])(=[O:20])=[O:19])#[N:16]

Participants

Reactant 2

HCID 334987-Aminodeacetoxycephalosporanic acid

HCID 23470093Cyanomethylsulfonylacetic acid

Product 1

HCID 681402357-Cyanomethylsulfonylacetamido-3-methyl-3-cephem-4-carboxylic acid

Procedure

When the t-butyl ester of 7-ADCA is acylated with cyanomethylsulfonylacetic acid by the procedure of Example 5, 7-cyanomethylsulfonylacetamido-3-methyl-3-cephem-4-carboxylic acid is obtained.

Sources & evidence

ORD record: ord-9b98ced3a0d84887a34e17ef38853317
Source dataset: uspto-grants-1976_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03963709

Reaction notes

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