m-Chloroperbenzoic acid → HCID 70594531, compound

HRID 1395504Notes

Reaction equation

HRID 1395504 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Br:12][C:13]1([CH3:40])[CH:18]([C:19]([O:21][CH2:22][C:23]([Cl:26])([Cl:25])[Cl:24])=[O:20])[N:17]2[C:27](=[O:39])[CH:28]([NH:29][C:30](=[O:38])[CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@H:16]2[S:15][CH2:14]1>C(Cl)(Cl)Cl>[Br:12][C:13]1([CH3:40])[CH:18]([C:19]([O:21][CH2:22][C:23]([Cl:24])([Cl:25])[Cl:26])=[O:20])[N:17]2[C:27](=[O:39])[CH:28]([NH:29][C:30](=[O:38])[CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@H:16]2[S:15](=[O:9])[CH2:14]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 70361012HCID 70361012, compound

Product 1

HCID 70594531HCID 70594531, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of m-chloroperbenzoic acid (0.445 g) in chloroform (5 ml) was added to a solution of 2,2,2-trichloroethyl 3-bromo-3-methyl-7-(2-phenylacetamido)cepham-4-carboxylate (1.21 g) under stirring at -5° to -10° C., and the mixture was stirred for an hour at the same temperature. After the reaction, the reaction mixture was washed with 5% sodium bicarbonate aqueous solution and with water in turn and then dried. After the solvent was distilled off, the residue was crystallized by adding ether. Thus obtained crystals were recrystallized from ethanol to give 2,2,2-trichloroethyl 3-bromo-3-methyl-7-(2-phenylacetamido)cepham-4-carboxylate-1-oxide (1.10 g), mp 159° to 161° C.

Workup

  1. stirringthe mixture was stirred for an hour at the same temperature
  2. customAfter the reaction
  3. washthe reaction mixture was washed with 5% sodium bicarbonate aqueous solution and with water in turn
  4. customdried
  5. distillationAfter the solvent was distilled off
  6. customthe residue was crystallized
  7. additionby adding ether
  8. customThus obtained crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-62402055ead349aebe9555511c67c94b
Source dataset
uspto-grants-1980_05
Patent number
US04203897

Reaction notes

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