Trifluoroacetic acid → N-hydroxy-2-(R)-[(4-methoxybenzenesulfonyl)(4-picolyl)amino]-2-[(N-(2-(2,3-methylenedioxyphenyl)-ethoxycarbonyl))-4-piperidinyl]acetamide trifluoroacetic acid salt

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(trityloxy)-2-(R)-[(4-methoxybenzenesulfonyl) (4-picolyl)amino]-2-[(N-(2-(2,3-methylenedioxyphenyl)-ethoxycarbonyl))-4-piperidinyl]acetamide (468 mg, 0.54 mmol) in methylene chloride (10 ml) cooled to 0° C. is added triethyl silane (0.17 ml, 1.08 mmol) followed by slow addition of trifluoroacetic acid (0.33 ml, 4.31 mmol). After stirring at 0° C. for 5 minutes, the solvent is removed in vacuo, at room temperature. The resulting white solid is dried on high vacuum for 1 hour and dissolved in the minimum amount of methylene chloride (ca. 2.5 ml). A mixture of diethyl ether (ca. 5 ml) and pentane (ca. 2.5 ml) is slowly added and the resulting white precipitate is triturated, filtered and washed with pentane (Note: this precipitation process must be repeated a second time if high purity is not obtained after the first attempt), to provide N-hydroxy-2-(R)-[(4-methoxybenzenesulfonyl)(4-picolyl)amino]-2-[(N-(2-(2,3-methylenedioxyphenyl)-ethoxycarbonyl))-4-piperidinyl]acetamide trifluoroacetic acid salt.

Provenance & Evidence