Water → Benzhydryl 7-phenylacetamido-3-[2-(2-pyridyl)vinyl]-3-cephem-4-carboxylate-1-oxide

HRID 464213Notes

Reaction equation

HRID 464213 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([O:10]O)=O)[CH:3]=1.C([C:25]1[S:26][C@@H:27]2[CH:43]([NH:44][C:45](=[O:53])[CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:42](=[O:54])[N:28]2[CH:29]([C:39](O)=[O:40])[C:30]=1[CH:31]=[CH:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=1)(C1C=CC=CC=1)C1C=CC=CC=1.[OH2:55]>ClCCl>[C:47]1([CH2:46][C:45]([NH:44][CH:43]2[C:42](=[O:54])[N:28]3[C:29]([C:39]([O:10][CH:8]([C:4]4[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=4)[C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:40])=[C:30]([CH:31]=[CH:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=4)[CH2:25][S:26](=[O:55])[C@H:27]23)=[O:53])[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 131714362Benzhydryl 7-phenylacetamido-3-[2-(2-pyridyl)vinyl]-2-cephem-4-carboxylic acid

Product 1

HCID 131714361Benzhydryl 7-phenylacetamido-3-[2-(2-pyridyl)vinyl]-3-cephem-4-carboxylate-1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of m-chloroperbenzoic acid (9.73 g) in dichloromethane (60 ml) was added dropwise to a solution of benzhydryl 7-phenylacetamido-3-[2-(2-pyridyl)vinyl]-2-cephem-4-carboxylic acid (trans isomer) (27.6 g) in dichloromethane (280 ml) at -25° to -30° C. and the solution was stirred for 10 minutes at the same temperature. The reaction mixture was poured into water (100 ml). The separated organic layer was washed with 2% aqueous sodium bicarbonate and brine, dried over magnesium sulfate and evaporated to give benzhydryl 7-phenylacetamido-3-[2-(2-pyridyl)vinyl]-3-cephem-4-carboxylate-1-oxide (trans isomer) (24.5 g)

Workup

  1. washThe separated organic layer was washed with 2% aqueous sodium bicarbonate and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-115275747092454d8c6e65821587f806
Source dataset
uspto-grants-1985_10
Patent number
US04546101

Reaction notes

Loading…