Hydrochloric Acid → methanesulfonic acid (2S,4R)-1-(naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidin-2-ylmethyl ester

Participants

Reaction Steps

A solution of 14.14 g (25 mmol) of (2S,4R)-[1-(naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidin-2-yl]-methanol in 300 ml CH2Cl2 was treated at 0° C. with 2.14 ml (27.7 mmol) methane sulfonylchloride, 3.02 ml (37.5 mmol) pyridine, 3.05 g (25 mmol) DMAP and stirred at room temperature for 4 h. The reaction mixture was poured into EtOAc/H2O acidified with 1 N HCl. The organic phase was washed with 10% aqueous NaCl, dried over Na2SO4 and evaporated to give 15.98 g (99%) of methanesulfonic acid (2S,4R)-1-(naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidin-2-ylmethyl ester, MS: 644 (MH+).

Provenance & Evidence