Methyl N-(triethylammoniosulfonyl)carbamate → HCID 68291990, compound

Participants

Reaction Conditions

Reaction Steps

Burgess reagent (1.35 g, 5.66 mmol) was added in one portion to a solution of (S)-methyl 2-((2R,3R)-3-((tert-butoxycarbonyl)amino)-2-ethylbutanamido)-3-hydroxypropanoate (1.71 g, 5.14 mmol) in anhydrous THF (79 ml) under a nitrogen atmosphere. The reaction was then allowed to stir at 60° C. for about 4 hr. TLC indicated complete consumption of starting material and a less polar spot (1:1 hexane:ethyl acetate; KMnO4 staining). After cooling to 0° C., saturated aqueous sodium bicarbonate solution (30 mL) was added and the mixture extracted with ethyl acetate (3×25 mL). The combined organics were then dried (MgSO4) and evaporated in vacuo to give (S)-methyl 2-((2R,3R)-2-((tert-butoxycarbonyl)amino)pentan-3-yl)-4,5-dihydrooxazole-4-carboxylate (1.62 g, 5.14 mmol, 100% yield) as an oil which was used immediately in the next step.

Provenance & Evidence