Methanol → HCID 22242831, compound

To a solution of 1-(4-carbamoyl-1,3-oxazol-2-yl)-3-hydroxyazetidine (423 mg, 2.31 mmol) (obtained as described in Reference Example 22(2)) in a mixture of methylene chloride (10 ml) and pyridine (30 ml) were added methanesulfonyl chloride (0.90 ml,11.55 mmol) and triethylamine (1.60 ml, 11.55 mmol) in an ice bath. After stirring the mixture in the ice bath for 10 minutes, the mixture was stirred at room temperature for 2 hours. After checking the completion of the reaction, methanol (1 ml) was added to the reaction mixture in an ice bath and then the resulting mixture was stirred at room temperature for 30 minutes. 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-carbamoyl-1,3-oxazol-2-yl)-3-methanesulfonyloxyazetidine (470 mg, yield 78%) as a white 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. customthe completion of the reaction
4. concentrationthe reaction mixture was concentrated under reduced pressure
5. customThe residue was purified by chromatography on a silica gel column

ORD record

ord-67531107207144beb29ca8f90a32c952

Source dataset

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07001897B2