Tetrabutylammonium Fluoride → N-(2-Amino-2-oxoethyl)-2-(3-hydroxy-1-azetidinyl)-N-(1-methylethyl)-4-thiazolecarboxamide

Participants

Reaction Steps

To a solution of 3-t-butyldiphenylsilyloxy-1-[4-(N-carbamoylmethyl-N-isopropyl-carbamoyl)-1,3-thiazol-2-yl]azetidine (6.52 g, 11.8 mmol) (obtained as described in Reference Example 49(3)) in anhydrous tetrahydrofuran (326 ml) was added a 1.0M solution of tetra-n-butylammonium fluoride in tetrahydrofuran (14.2 ml, 14.2 mmol) in an ice bath, and the mixture was stirred in the ice bath for 2 hours. After checking the completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using ethyl acetate:methanol (10:1) as the eluant to afford 1-[4-(N-carbamoylmethyl-N-isopropyl-carbamoyl)-1,3-thiazol-2-yl]-3-hydroxyazetidine (2.35 g, yield 67%) as a white solid.

Provenance & Evidence