m-Chloroperbenzoic acid → HCID 20429039, compound

HRID 615115Notes

Reaction equation

HRID 615115 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:19](=[O:20])[N:18]2[CH:13]1[S:14][CH2:15][N:16]([S:31]([C:34]([F:37])([F:36])[F:35])(=[O:33])=[O:32])[CH:17]2[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:46])C=1>C(Cl)Cl>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:19](=[O:20])[N:18]2[CH:13]1[S:14](=[O:46])[CH2:15][N:16]([S:31]([C:34]([F:35])([F:36])[F:37])(=[O:32])=[O:33])[CH:17]2[C:21]([O:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:22])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 14230826HCID 14230826, compound

Product 1

HCID 20429039HCID 20429039, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of benzyl 7-phenoxyacetamido-8-oxo-3-trifluoromethanesulfonyl-5-thia-1,3-diazabicyclo[4,2,0]octane-2-carboxylate (1.172 g.) in methylene chloride (10 ml.) was added dropwise a solution of m-chloroperbenzoic acid (430 mg.) in methylene chloride (6 ml.) at 0° C. with stirring over a period of 20 minutes, and the mixture was stirred for an additional 15 minutes. The mixture was diluted with methylene chloride and washed with a chilled dilute aqueous solution of sodium bicarbonate and a mixture of a dilute aqueous solution of sodium chloride and an aqueous solution of sodium bicarbonate. Drying over magnesium sulfate and removal of the solent left an amorphous solid (1.2 g.), which was chromatographed on silica gel (17 g.) with methylene chloride and then a mixed solvent of methylene chloride and ethyl acetate as an eluent to give an amorphous solid (1.10 g.) of benzyl 7-phenoxyacetamido-8-oxo-3-trifluoromethanesulfonyl-5-thia-1,3-diazabicyclo[4,2,0]octane-2-carboxylate-5-oxide.

Workup

  1. stirringthe mixture was stirred for an additional 15 minutes
  2. washwashed with a chilled dilute aqueous solution of sodium bicarbonate
  3. additiona mixture of a dilute aqueous solution of sodium chloride
  4. dry with materialDrying over magnesium sulfate and removal of the
  5. waitsolent left an amorphous solid (1.2 g.), which
  6. customwas chromatographed on silica gel (17 g.) with methylene chloride

Sources & evidence

ORD record
ord-e74b26bac90e4bd7b4232cfc1578de70
Source dataset
uspto-grants-1985_02
Patent number
US04497738

Reaction notes

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