Triethylamine → HCID 22242733, compound

Participants

Reaction Steps

To a solution of 1-[4-(N-carbamoylmethyl-N-isopropyl-carbamoyl)-1,3-thiazol-2-yl]-3-hydroxyazetidine (2.35 g, 7.88 mmol) (obtained as described in Reference Example 49(4)) in methylene chloride (120 ml) were added methanesulfonyl chloride (0.91 ml, 11.8 mmol) and triethylamine (1.66 ml, 11.8 mmol) in an ice bath. The reaction mixture was stirred in the ice bath for 2 hours. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The obtained organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and 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-methanesulfonyloxyazetidine (516 mg, yield 17%) as a pale yellow solid and 1-[4-(cyanomethyl-isopropyl-carbamoyl)-1,3-thiazol-2-yl]-3-methanesulfonyloxyazetidine (634 mg, yield 22%) as a pale yellow solid.

Provenance & Evidence