Methanol → HCID 22242775, compound

To a solution of 1-(4-cyano-1,3-oxazol-2-yl)-3-hydroxyazetidine (214 mg, 1.30 mmol) (obtained as described in Reference Example 23(2)) in a mixture of methylene chloride (10 ml) and pyridine (5 ml) were added methanesulfonyl chloride (0.50 ml, 6.50 mmol) and triethylamine (0.90 ml, 6.50 mmol) in an ice bath. After stirring the mixture in the ice bath for 10 minutes, the resulting mixture was stirred at room temperature for 2 hours. After checking the completion of the reaction, methanol (1 ml) was added thereto 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 as the eluant to afford 1-(4-cyano-1,3-oxazol-2-yl)-3-methanesulfonyloxyazetidine (310 mg, yield 98%) as a colorless oil.

1. additionwas added
2. stirringin an ice bath and then the 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-f2a203564d6a475cbb0e5d1742da9293

Source dataset

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07001897B2