m-Chloroperbenzoic acid → HCID 13649352, compound

HRID 1200158Notes

Reaction equation

HRID 1200158 reaction equation
[C:1]([N:9]1[C@H:13]([C:14](=[O:24])[NH:15][C@H:16]([CH3:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][S@@:11](=[O:25])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:34])C=1>C(Cl)Cl>[C:1]([N:9]1[C@H:13]([C:14](=[O:24])[NH:15][C@H:16]([CH3:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][S:11](=[O:34])(=[O:25])[CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13649349HCID 13649349, compound

Product 1

HCID 13649352HCID 13649352, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 357 mg of (1R,4R)-3-benzoyl-4-[(R)-α-methylbenzylcarbamoyl]-1-oxothiazolidine (prepared as described in Example 25 or 28 ) in 10 ml of methylene chloride were added 203 mg of 85% m-chloroperbenzoic acid, and the mixture was stirred at room temperature for 20 hours. The reaction mixture was then washed, in turn, with 30 ml of a 4% aqueous solution of sodium bicarbonate and with 30 ml of water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to leave an oil, which was then subjected to column chromatography through 80 g of silica gel, eluted with a 97.5:2.5 by volume mixture of methylene chloride and ethanol, to give an oil. This oil was crystallized by the addition of benzene to give 266 mg of the title compound in the form of crystals. The physical properties of these crystals were identical with those of the compound obtained as described in Example 27.

Workup

  1. washThe reaction mixture was then washed, in turn, with 30 ml of a 4% aqueous solution of sodium bicarbonate and with 30 ml of water
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customto leave an oil, which
  5. washeluted with a 97.5:2.5 by volume mixture of methylene chloride and ethanol
  6. customto give an oil
  7. customThis oil was crystallized by the addition of benzene

Sources & evidence

ORD record
ord-8e51e3a175b94a5b9aca2f765150a985
Source dataset
uspto-grants-1990_02
Patent number
US04904680

Reaction notes

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