Water → HCID 131713531, compound

HRID 1262752Notes

Reaction equation

HRID 1262752 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:36](=[O:37])[N:13]3[C:14]([C:20]([O:22][CH:23]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[S:21])=[C:15]([CH3:19])[CH2:16][S:17](=O)[C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC=C(C)C.C(Br)(=O)C.O>C(Cl)Cl>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:36](=[O:37])[N:13]3[C:14]([C:20]([O:22][CH:23]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)=[S:21])=[C:15]([CH3:19])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10482Acetyl bromideHCID 105532-Methyl-2-buteneHCID 131713532HCID 131713532, compound

Product 1

HCID 131713531HCID 131713531, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzhydryl 7-phenylacetamido-3-methylthio-3-cephem-4-carboxylate-1-oxide (6.5 g) and amylene (2.53 ml) in methylenechloride (100 ml) was dropwise added acetyl bromide (2.4 ml) under ice-cooling with stirring. The mixture was stirred at ambient temperature for 30 minutes. The resultant solution was added to water. The separated organic layer was washed with a saturated aqueous solution of sodium chloride twice and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give benzhydryl 7-phenylacetamido-3-methylthio-3-cephem-4-carboxylate (5.4 g).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at ambient temperature for 30 minutes
  3. washThe separated organic layer was washed with a saturated aqueous solution of sodium chloride twice
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-24e2a24530b149498f431dbfbe265889
Source dataset
uspto-grants-1984_06
Patent number
US04452851

Reaction notes

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