Triphenylphosphine → HCID 54356307, compound

HRID 343624Notes

Reaction equation

HRID 343624 reaction equation
[O:1]=[O+][O-].[C:4]([O:8][C:9](=[O:28])[CH2:10][N:11]([S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)(=[O:19])=[O:18])[CH2:12][CH:13]=C(C)C)([CH3:7])([CH3:6])[CH3:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl.CO>[C:4]([O:8][C:9](=[O:28])[CH2:10][N:11]([S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)(=[O:18])=[O:19])[CH2:12][CH:13]=[O:1])([CH3:5])([CH3:6])[CH3:7]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24823OzoneHCID 53702490HCID 53702490, compound

Product 1

HCID 54356307HCID 54356307, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Ozone is passed through a solution of [(4-methoxybenzenesulfonyl)-(3-methyl-but-2-enyl)-amino]-acetic acid t-butyl ester (2.0 grams, 5.4 mmol) in methylene chloride-methanol (50 mL, ca. 1:1) at -78° C. until a blue color persisted. Triphenylphosphine (4.24 grams, 16.2 mmol) is added and the resulting solution is stirred at room temperature for 3 hours. Concentration provided the crude product which is purified by silica gel chromatography (elution with 1:1 ethyl acetate-hexanes) to provide [(4-methoxybenzenesulfonyl)-(2-oxo-ethyl)-amino]-acetic acid t-butyl ester.

Workup

  1. concentrationConcentration
  2. customprovided the crude product which
  3. customis purified by silica gel chromatography (elution with 1:1 ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-65a2db30a28b42dcabd65f3751fbb731
Source dataset
uspto-grants-1999_01
Patent number
US05861510

Reaction notes

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