Cyanomethylthioacetyl chloride → 7-Cyanomethylthioacetamido-3-cephem-3ol-4-carboxylic acid p-nitrobenzyl ester

HRID 1287607Notes

Reaction equation

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

Participants

Reactant 2

HCID 19989189Cyanomethylthioacetyl chloride

HCID 681232354-Nitrobenzyl 7-amino-3-hydroxy-3-cephem-4-carboxylate

Product 1

HCID 1317104857-Cyanomethylthioacetamido-3-cephem-3ol-4-carboxylic acid p-nitrobenzyl ester

Procedure

7-Amino-3-hydroxy-3-cephem-4-carboxylic acid p-nitrobenzyl ester [J. Am. Chem. Soc. 96, 4986 (1974)]is acylated with cyanomethylthioacetyl chloride by the procedure described in Example 1 to obtain 7-cyanomethylthioacetamido-3-cephem-3-ol-4-carboxylic acid p-nitrobenzyl ester as an oil.

Sources & evidence

ORD record: ord-dd8f51ab655c49c6849def2d308d1699
Source dataset: uspto-grants-1976_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03985746

Reaction notes

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