Triethylamine → HCID 178474821, compound

Participants

Reaction Steps

Following the general procedure for phosphorylation of Description 23, (methylethoxycarbonyloxy)ethyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-hydroxy-butanoate (40) (0.88 g, 2.0 mmol) dissolved in 10 mL of anhydrous dichloromethane (DCM) was reacted with 0.58 mL (1.6 g, 6.0 mmol) of diphenyl chlorophosphate [(PhO)2POCl] in the presence of 4-(N,N-dimethylamino)pyridine (DMAP) (0.12 g, 1.0 mmol) and triethylamine (TEA) (0.84 mL, 0.61 g, 6.0 mmol). The reaction was monitored by TLC. After aqueous work-up, the crude material was further purified by silica gel column chromatography using ethyl acetate (EtOAc) as eluent to provide 1.1 g (81% yield) of the title compound (52a) as a colorless oil. Rf=0.45 (EtOAc). 1H NMR (400 MHz, CDCl3, both diastereomers): δ=1.08-1.09 (2s, 3H), 1.12-1.13 (2s, 3H), 1.25-1.32 (m, 6H), 1.44-1.50 (2d, J=5.6, 5.6 Hz, 3H), 1.85 (s, 3H), 1.99-2.06 (m, 2H), 3.13-3.18 (m, 2H), 3.28-3.32 (m, 2H), 3.98-4.05 (m, 2H), 4.82-4.91 (m, 2H), 6.38-6.42 (br. m, 1H), 6.79-6.85 (m, 1H), 7.15-7.23 (m, 6H), 7.30-7.38 (m, 4H) ppm. MS (ESI) m/z 674.19 (M+H)+, 696.09 (M+Na)+. The analytical data was consistent with the proposed structure.

Provenance & Evidence