Methanesulfonyl chloride → (1R)-2-{[(Benzyloxy)carbonyl]amino}-1-[(4-cyanophenoxy)methyl]ethyl Methanesulfonate

Participants

Reaction Conditions

Reaction Steps

4-(Dimethylamino)pyridine (0.22 g, 1.77 mmol) was added to a solution of benzyl (2R)-3-(4-cyanophenoxy)-2-hydroxypropylcarbamate (see step (iii) above; 5.79 g, 17.7 mmol) in pyridine (15 mL). The mixture was cooled to 0° C., and methanesulfonyl chloride (2.23 g, 19.5 mmol) was added slowly at 0° C. The mixture was allowed to reach rt, at which temperature it was then stirred for 4 h. The solvent was evaporated. DCM (100 mL) was added, washed with water, 1 N H2SO4 and brine, dried (Na2SO4) and evaporated giving 6.0 g (84%) of a yellow oil.

Provenance & Evidence