Dichloromethane → HCID 12136230, compound

Participants

Reaction Conditions

Reaction Steps

A solution of tetramethylammonium triacetoxyborohydride (263 mg, 1 mmol, 10 eq) in MeCN/HOAc(1:1, 1.1 mL) is stirred for 1 h at 23° C. and cooled to −30° C. A solution of (2R,3S,4R,7S,8Z,10S, 11S,12S,13Z, 16S,17R,18R, 19S,20S)-19-[(aminocarbonyl)oxy]-3,11,17-tris[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7-hydroxy-N-methoxy-N,2,4,10,12,14,16,18,20-nonamethyl-5-oxo-21-(phenylmethoxy)-8,13-heneicosadienamide (103 mg, 0.1 mmol)in MeCN (1 mL) is added dropwise. The mixture is stirred for 14 h at −30° C. Saturated Rochelle's salt solution is added and the resultant stirred for 30 min. Then the mixture is warmed to 23° C. CH2Cl2 (5 mL) is added to the mixture. The organic layer is separated, washed with brine and dried over MgSO4. The solvent is removed. The crude product is chromatographed (20% EtOAc in hexane) to give 80 mg (80%) of the desired compound as a colorless oil.

Provenance & Evidence