m-Chloroperbenzoic acid → HCID 11121760, compound

HRID 1490347Notes

Reaction equation

HRID 1490347 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[Si:12]([O:19][C@@H:20]([C@@H:22]1[C@@H:25]([S:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[NH:24][C:23]1=[O:33])[CH3:21])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]>C(Cl)Cl>[Si:12]([O:19][C@@H:20]([C@@H:22]1[C@@H:25]([S:26]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[O:6])[NH:24][C:23]1=[O:33])[CH3:21])([C:15]([CH3:18])([CH3:16])[CH3:17])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 11089029HCID 11089029, compound

Product 1

HCID 11121760HCID 11121760, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.5 g of 3-chloroperoxybenzoic acid was added, whilst ice-cooling, to a solution of 2 g of (3S,4R)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-phenylthio-2-azetidinone [prepared as described in step (i) above] in 30 ml of methylene chloride, and the resulting mixture was stirred at room temperature for 6 hours. At the end of this time, the reaction mixture was mixed with 30 ml of methylene chloride, and the organic layer was separated and washed with water, with a saturated aqueous solution of sodium hydrogencarbonate and again with water, in that order. It was then dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by flash chromatography, using a 1:1 by volume mixture of cyclohexane and ethyl acetate as the eluent, to give 1.9 g of the title compound consisting of two diastereomers, differing in the configuration of the sulfoxide group, as colorless crystals, melting at 65°-70° C.

Workup

  1. customthe organic layer was separated
  2. washwashed with water, with a saturated aqueous solution of sodium hydrogencarbonate and again with water, in that order
  3. dry with materialIt was then dried over anhydrous magnesium sulfate
  4. customthe solvent was removed by distillation under reduced pressure
  5. customThe resulting residue was purified by flash chromatography
  6. additionby volume mixture of cyclohexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-a352c756318f47e9ae6ad902f0e48437
Source dataset
uspto-grants-1997_10
Patent number
US05681951

Reaction notes

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