Methanol → HCID 86590853, compound

To a solution of (3R)-1-(4-carbamoyl-1,3-thiazol-2-yl)-3-hydroxypyrrolidine (290 mg, 1.36 mmol) (obtained as described in Reference Example 18(6)) suspended in methylene chloride (9 ml) were added methanesulfonyl chloride (0.684 ml, 8.85 mmol) and triethylamine (1.24 ml, 8.85 mmol) in an ice bath. After stirring the mixture in the ice bath for 10 minutes, the mixture was stirred at room temperature overnight. After checking the completion of the reaction, methanol (0.33 ml) was added to the reaction mixture in an ice bath, and then the resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using 5% methanol in ethyl acetate→10% methanol in ethyl acetate as the eluant to afford (3R)-1-(4-carbamoyl-1,3-thiazol-2-yl)-3-methanesulfonyloxypyrrolidine (148 mg, yield 40%) as a pale yellow solid.

1. additionwas added to the reaction mixture in an ice bath
2. stirringthe resulting mixture was stirred at room temperature for 30 minutes
3. concentrationThe reaction mixture was concentrated under reduced pressure
4. customThe residue was purified by chromatography on a silica gel column

ORD record

ord-602902d796a542f797a9ce6ee5015140

Source dataset

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07001897B2