Ammonium Chloride → HCID 58844429, compound

Participants

Reaction Steps

To a solution of (3-{[(2R,3S)-3-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-oxoazetidin-2-yl]acetyl}phenyl)acetic acid (2.62 g) prepared in reference example 16, 4-dimethylaminopyridine (78 mg) and 2.0M methylamine/THF (3.3 ml) in dichloromethane (25 ml) was added at 0° C. 1-ethyl-3-(dimethylaminopropyl)carbodiimide hydrochloride (1.24 g) and the mixture was stirred for 6 hours. Further, 1-ethyl-3-(dimethylaminopropyl)carbodiimide hydrochloride (0.13 g) and 2.0M methylamine/THF (0.33 ml) were added thereto and the mixture was reacted overnight. To the mixture was added an aqueous saturated ammonium chloride solution (50 ml) and the mixture was extracted with ethyl acetate.(100 ml). The organic layer was washed with a saturated aqueous sodium chloride solution (2×50 ml), dried over magnesium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (chloroform/methanol) to give 2-(3-{[(2R,3S)-3-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-oxoazetidin-2-yl]acetyl}phenyl)-N-methylacetamide (1.96 g).

Provenance & Evidence