Methanesulfonyl chloride → 1-Tert-butoxycarbonylamino-2-(2-methanesulfonyloxyethyl)cyclopropanecarboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

1-tert-Butoxycarbonylamino-2-(2-hydroxyethyl)-cyclopropanecarboxylic acid methyl ester (0.500 g, 1.93 mmol, from Example 104) was diluted in 8 mL DCM and cooled to 0° C. under an Ar atmosphere. TEA (0.54 mL, 3.9 mmol) and methanesulfonyl chloride (0.30 mL, 3.9 mmol) were added sequentially. After 2.5 h, the solvent was removed in vacuo and the residue taken up in EtOAc and H2O (15 mL each). The aqueous layer was extracted with 3×10 mL EtOAc. The combined organics were washed with brine and dried over anhydrous MgSO4. Following concentration in vacuo, the residue was purified by column chromatography on SiO2 (0 to 50% Hex/EA) to produce 1-tert-butoxycarbonylamino-2-(2-methanesulfonyloxyethyl)cyclopropanecarboxylic acid methyl ester (0.55 g, 84%). LCMS found 360.1 [M+Na]+.

Provenance & Evidence