Triethylamine → HCID 178473650, compound

Participants

Reaction Steps

Following the general procedure for phosphorylation of Description 23, (ethoxycarbonyloxy)ethyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-hydroxy-butanoate (32) (0.43 g, 1.0 mmol) dissolved in 10 mL of anhydrous dichloromethane (DCM) was reacted with 0.58 mL (0.67 g, 2.5 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) (0.35 mL, 0.25 g, 2.5 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 0.43 g (65% yield) of the title compound (51a) as a colorless oil. Rf=0.45 (EtOAc). 1H NMR (400 MHz, CDCl3, both diastereomers): δ=1.09-1.10 (2s, 3H), 1.12-1.13 (2s, 3H), 1.26-1.32 (m, 3H), 1.45-1.52 (2d, J=5.6, 5.6 Hz, 3H), 1.86-1.87 (2s, 3H), 2.01-2.06 (m, 2H), 3.15-3.17 (m, 2H), 3.39-3.34 (m, 2H), 3.98-4.05 (m, 2H), 4.15-4.22 (m, 3H), 4.87-4.91 (2d, J=7.6, 7.6 Hz, 1H), 6.30-6.34 (br. m, 1H), 6.81-6.83 (m, 1H), 7.18-7.26 (m, 6H), 7.33-7.38 (m, 4H) ppm. MS (ESI) m/z 660.11 (M+H)+, 681.94 (M+Na)+. The analytical data was consistent with the proposed structure.

Provenance & Evidence