Water → Methyl 2-[(4'-methoxy[1,1'-biphenyl]-4-yl)sulfonyl]amino-4,5-epoxypentanoate

Participants

Reaction Steps

To a solution of methyl 2-[(4′-methoxy[1,1′-biphenyl]-4-yl)sulfonylamino]-pent-4-enoate 1(15.3 g, 40.8 mmol) in CH2Cl2(150 mL), NaHCO3 (7.1 g, 85 mmol) and water (80 mL) at 0° C., is added slowly m-chloroperbenzoic acid (32.6 g, ˜123 mmol, 57-86%). The reaction mixture is stirred overnight. The reaction is then diluted with aqueous NaHCO3 and the mixture is extracted three times with EtOAc. The combined EtOAc layer is washed with NaHCO3, brine, dried over MgSO4 and concentrated to an oil. Purification is accomplished by column chromatography with EtOAc/hexane (3:7 to 6:4) as the eluent to give the desired product as a mixture of two isomers (ratio 2:3).

Provenance & Evidence