Dimethyl Sulfoxide → HCID 22862589, compound

Participants

Reaction Steps

A sulfur trioxide-pyridine complex (985 mg) was added to a solution of (S)-2-[[(S)-2-[3-(tert-butyldimethylsilyloxy)-1-hydroxypropyl]-1-pyrrolidinyl]carbonyl]-N-(phenylmethyl)-1-pyrrolidinecarboxamide (1.01 g) in a mixture of toluene (2 ml), DMSO (3 ml) and triethyl amine (0.94 ml), under ice-cooling, and the mixture was stirred for 3 hours. The reaction mixture was poured into ice water, and extracted with ethyl acetate. The organic layer was washed with 10% citric acid, water, saturated sodium hydrogencarbonate, 1% hypochlorous acid, and water in order, dried over anhydrous sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (eluent: chloroform-methanol) to give (S)-2[[(S)-2-[3-(tert-butyldimethylsilyloxy)-1-oxopropyl]-1-pyrrolidinyl]carbonyl]-N-(phenylmethyl)-1-pyrrolidinecarboxamide (374 mg) and the title compound (280 mg) (see Table 5).

Provenance & Evidence