Sodium borohydride → 3-Hydroxy-7beta-phenoxyacetylamino-cepham-4alpha-carboxylic acid diphenylmethyl ester

HRID 1155335Notes

Reaction equation

HRID 1155335 reaction equation
[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:36])[C@@H:24]([NH:25][C:26](=[O:35])[CH2:27][O:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C@H:21]3[S:20][CH2:19][C:18]=2[OH:37])=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CN(C)C=O.C(O)(=O)C>[C:1]1([CH:7]([O:14][C:15]([C@@H:17]2[N:22]3[C:23](=[O:36])[C@@H:24]([NH:25][C:26](=[O:35])[CH2:27][O:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C@H:21]3[S:20][CH2:19][CH:18]2[OH:37])=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 547082513-Hydroxy-7beta-phenoxyacetylamino-3-cephem-4-carboxylic acid diphenylmethyl ester

Product 1

HCID 705700963-Hydroxy-7beta-phenoxyacetylamino-cepham-4alpha-carboxylic acid diphenylmethyl ester

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

In the same manner as that described under (a), 111 g of 3-hydroxy-7β-phenoxyacetylamino-3-cephem-4-carboxylic acid diphenylmethyl ester (crude product) in a mixture of 640 ml of dimethylformamide and 160 ml of glacial acetic acid are reduced with 4.5 g of sodium borohydride and worked up. The title compound having the properties mentioned under (a) is obtained.

Sources & evidence

ORD record
ord-bdcf75c5a5fb419f802979c238d46a71
Source dataset
uspto-grants-1981_11
Patent number
US04301279

Reaction notes

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