Methanesulfonyl chloride → HCID 89315659, compound

Participants

Reaction Steps

To a solution of (3aS,4R,5R,6R,7aS)-4,5-bis(benzyloxy)-6-(hydroxymethyl)hexahydrobenzo[d]oxazol-2(3H)-one (1.86 g, 4.86 mmol) in pyridine (11 mL) at −20° C. was added MeSO2Cl (0.723 g, 6.31 mmol). The mixture was slowly warmed to room temperature and stirred for 4 h. The reaction was diluted with aqueous saturated NH4Cl (100 mL) and extracted with EtOAc (2×60 mL). The extracts were washed with 0.5 N HCl (3×60 mL), dried with MgSO4. The solvent was evaporated to give ((3aS,4R,5R,6R,7aS)-4,5-bis(benzyloxy)-2-oxooctahydrobenzo[d]oxazol-6-yl)methyl methanesulfonate as a white solid (2.25 g, 100%) which was pure enough for next reaction. MS m/z 484.1 (M+23, 100%); 1H NMR (400 MHz, CDCl3) δ 7.30-7.44 (m, 10H), 4.92 (d, J=11.9 Hz, 1H), 4.87 (d, J=11.1 Hz, 1H), 4.66-4.70 (m, 2H), 4.65 (d, J=11.0 Hz, 1H), 4.57 (d, J=11.9 Hz, 1H), 4.43 (dd, J=9.7 Hz, 4.2 Hz, 1H), 4.21 (dd, J=9.7 Hz, 3.0 Hz, 1H), 3.59 (t, J=6.8 Hz, 1H), 3.51 (t, J=7.6 Hz, 1H), 3.41 (t, J=8.9 Hz, 1H), 2.12-2.26 (m, 2H), 1.79-1.87 (m, 1H).

Provenance & Evidence