Benzyl mercaptan → 3-[(4'-Methoxy[1,1'-biphenyl]-4-yl)sulfonyl]amino-2-oxo-5-[(benzylthio)methyl]-tetrahydrofuran

Temperatur

70 °C

To a solution of methyl 2-[(4′-methoxy[1,1′-biphenyl]-4-yl)sulfonyl]amino-4,5-epoxypentanoate 1d (0.5 g, 1.28 mmol) in benzene (3 mL), NaHCO3 (0.32 g, 3.84 mmol) and Et3N (0.23 mL, 1.6 mmol) at room temperature is added slowly benzyl mercaptan (0.62 mL, 4.99 mmol). The reaction mixture is heated at 70° C. for 3 h, and stirred two days at room temperature. The resulting mixture is diluted with water, and then the mixture is extracted three times with EtOAc. The combined EtOAc layer is washed with water, brine, dried over MgSO4 and concentrated to an oil which is purified by column chromatography eluting with hexane/EtOAc (4:1) to give the desired product.

1. extractionthe mixture is extracted three times with EtOAc
2. washThe combined EtOAc layer is washed with water, brine
3. dry with materialdried over MgSO4
4. concentrationconcentrated to an oil which
5. customis purified by column chromatography
6. washeluting with hexane/EtOAc (4:1)

ORD-Eintrag

ord-58e6714a78dc4ad880b5621a36a87da4

Quelldatensatz

uspto-grants-2003_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06566381B1