Reacción #534034

Ecuación de reacción

compound 93

(4aS,4bR,5S,6aS,6bS,9aR,10aS,12S)-8-Benzyl-4b,12-difluoro-5-hydroxy-4a,6a-dimethyl-2-oxo-2,4b,5,6,6a,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-aza-pentaleno[2,1-a]phenanthrene-6b-carboxylic acid

3-mercaptodihydrofuran-2(3H)-one

→

title compound

Rendimiento 13.1%

(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-8-Benzyl-4b,12-difluoro-5-hydroxy-4a,6a-dimethyl-2-oxo-2,4b,5,6,6a,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-aza-pentaleno[2,1-a]phenanthrene-6b-carbothioic acid S-(2-oxo-tetrahydro-furan-3-yl) ester

Rendimiento 13.1%

Disolventes

AcOEt

DMF

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITat 70° C. for 48 hours
2. 2
   Lavadowashed with brine
3. 3
   SecadoThe organic phase is dried over Na2SO4
4. 4
   Filtraciónfiltered
5. 5
   OtroThe solvent is evaporated
6. 6
   Otroto give a brown oil which
7. 7
   Otrois purified by silica gel chromatography (AcOEt/petroleum ether 45/55)

Procedimiento

A solution of compound 93 and 1,1-carbonyldiimidazole (74.3 mg, 0.458 mmol) in dry DMF (3 ml) is stirred under nitrogen at RT for 1 hour and at 65° C. for 1 hour 30 minutes. The mixture is cooled to RT and 4-dimethylaminopyridine (46.7 mg, 0.382 mmol) and a solution of 3-mercaptodihydrofuran-2(3H)-one (54.1 mg, 0.458 mmol) in dry DMF (1.2 ml) are added. The mixture is stirred at RT for 1 hour then at 70° C. for 48 hours. The mixture is diluted with AcOEt and washed with brine. The organic phase is dried over Na2SO4 and filtered. The solvent is evaporated to give a brown oil which is purified by silica gel chromatography (AcOEt/petroleum ether 45/55) to afford the title compound (30 mg, 0.050 mmol, 13.14% yield).

Fuente