Potassium Bromide → 7-Phenylacetamido-3-chloro-3-cephem-4-carboxylic acid

HRID 1735483Notes

Reaction equation

HRID 1735483 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:32](=[O:33])[N:13]3[C:14]([C:19]([O:21]CC4C=CC([N+]([O-])=O)=CC=4)=[O:20])=[C:15]([Cl:18])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[K+].[Br-]>>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:32](=[O:33])[N:13]3[C:14]([C:19]([OH:21])=[O:20])=[C:15]([Cl:18])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 253877Potassium BromideHCID 67655773p-Nitrobenzyl 7-phenylacetamido-3-chloro-3-cephem-4-carboxylate

Product 1

HCID 131931467-Phenylacetamido-3-chloro-3-cephem-4-carboxylic acidYield 40.2%

Procedure

The procedure described in Example 4 was repeated using p-nitrobenzyl 7-phenylacetamido-3-chloro-3-cephem-4-carboxylate as the starting material. The corresponding acid was obtained in 40.2% yield. M.p. 142°-145° C. IR (KBr) cm-1 : 3260, 1755, 1635, 1515, 680. NMR (DMSO-δ6) δ: 3.2-4.2 (m, 4 H, S--CH2 & Ar--CH2), 5.2 (d, 1 HS--CH), 5.7 (q, 1 H, N--CH), 7.3 (s, 5 H, Ar--H), 9.1 (d, 1 H, NH).

Workup

  1. customThe corresponding acid was obtained in 40.2% yield

Sources & evidence

ORD record
ord-4a655c2030464523941e1e8ad543397a
Source dataset
uspto-grants-1996_07
Patent number
US05536830

Reaction notes

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