Dimethyl Sulfoxide → HCID 54503003, compound

Participants

Reaction Steps

A solution of 0.18 ml oxalyl chloride in 10 ml CH2Cl2 is slowly treated at −60° C. with 0.33 ml DMSO. After 15 minutes stirring at −60° C. a cold solution (−78° C.) of 2-methyl-butyric acid 8-[5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-6-(4-methoxy-benzylcarbamoyl)-hexyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester in 5 ml CH2Cl2 is added. After 2 hours at −60° C., 0.80 ml of NEt3 is added and the temperature is slowly rised to room temperature. After 2 hours at room temperature the reaction is quenched with H2O. The phases are separated and the organic phase dried and concentrated. The crude product is purified by silica gel chromatography (CH2Cl2/MeOH). The resulting compound is dissolved in THF and treated with AcOH and Bu4NF.3H2O. After 30 hours the reaction mixture is concentrated, diluted with AcOEt and washed with H2O, sat. NaHCO3, brine, then dried (Na2SO4) and concentrated. The crude product is purified by silica gel chromatography. Pure fractions are combined and evaporated to afford 2-methyl-butyric acid 8-[5-hydroxy-6-(4-methoxy-benzylcarbamoyl)-3-oxo-hexyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester as foam.

Provenance & Evidence