Acetic Acid → 3-Hydroxy-1-[4-(methoxycarbonylaminomethyl)-1,3-thiazol-2-yl]azetidine

To a solution of 3-t-butyldiphenylsilyloxy-1-[4-(methoxycarbonylaminomethyl)-1,3-thiazol-2-yl]azetidine (1.88 g, 3.90 mmol) (obtained as described in Reference Example 63(1)) in anhydrous tetrahydrofuran (94 ml) were added acetic acid (0.27 ml, 4.68 mmol) and 1.0 M tetra-n-butylammonium fluoride in tetrahydrofuran (4.68 ml, 4.68 mmol) in an ice bath and the mixture was stirred in an ice bath for 30 minutes. After checking the completion of the reaction, the mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using ethyl acetate as the eluant to afford 3-hydroxy-1-[4-(methoxycarbonylaminomethyl)-1,3-thiazol-2-yl]azetidine (426 mg, yield 45%) as a white solid.

1. customthe completion of the reaction
2. customthe mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
3. washThe organic layer was washed with saturated aqueous sodium chloride solution
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by chromatography on a silica gel column

ORD record

ord-2d26c950649b47959200c8cbf95c3c59

Source dataset

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07001897B2