Hydrochloric Acid → (3R,5S)-allyloxycarbonyl-5-(5-chloroimidazo[5,1-b]thiazol-2-yl)methyl-3-hydroxypyrrolidine

A solution of 1.430 g of (3R,5S)-1-allyloxycarbonyl-3-t-butyldimethylsilyloxy-5-(5-chloroimidazo[5,1-b]thiazol-2-yl)methylpyrrolidine in 31.5 ml of dry acetonitrile is cooled to 3° C., 1.3 ml of concentrated hydrochloric acid is added dropwise thereto while maintaining the internal temperature at 4° C. or below, and the mixture is stirred in this state for 15 min. The reaction solution is diluted with 200 ml of ethyl acetate, washed with 40 ml of a 5% aqueous sodium hydrogencarbonate solution (aqueous layer pH 9) and dried over anhydrous magnesium sulfate. The solvent is removed by evaporation under reduced pressure to give a crude product which is then purified by column chromatography on silica gel (ethyl acetate) to give 1.020 g of (3R,5S)-allyloxycarbonyl-5-(5-chloroimidazo[5,1-b]thiazol-2-yl)methyl-3-hydroxypyrrolidine as a slightly yellow viscous material.

1. temperaturewhile maintaining the internal temperature at 4° C. or below
2. washwashed with 40 ml of a 5% aqueous sodium hydrogencarbonate solution (aqueous layer pH 9)
3. dry with materialdried over anhydrous magnesium sulfate
4. customThe solvent is removed by evaporation under reduced pressure
5. customto give a crude product which
6. customis then purified by column chromatography on silica gel (ethyl acetate)

ORD-Eintrag

ord-740a21f2de0c46dba004337e8e0328e3

Quelldatensatz

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06180622B2