Trifluoroacetic acid → HCID 24794622, compound

Participants

Reaction Steps

A sample of tert-butyl ((1S,2S,5R)-2-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-5-methoxycyclohexyl)methylcarbamate (0.75 g, 1.577 mmol) was dissolved in CH2Cl2 (15 mL) at room temperature. The solution was charged with trifluoroacetic acid (1.215 mL, 15.77 mmol) and stirred for 6 h. It was then evaporated and dried in vacuo. The residue was dissolved in EtOAc and washed with saturated Na2CO3, followed by brine. The organic layer was then dried over anhydrous Na2SO4, concentrated and dried in vacuo to yield a pale yellow foam. This material was dissolved in CH2Cl2 (10 mL) at room temperature. The solution was charged sequentially with triethylamine (0.659 mL, 4.73 mmol), dimethylaminopyridine (0.019 g, 0.158 mmol), and acetic anhydride (0.164 mL, 1.734 mmol). The reaction mixture was stirred for 90 min and then quenched with saturated NaHCO3. The reaction mixture was then extracted with CH2Cl2 (3×). The organic layers were combined, dried over anhydrous MgSO4, concentrated and chromatographed. The desired product, benzyl (S)-1-((1S,2S,4R)-2-(acetamidomethyl)-4-methoxycyclohexyl)-2-oxopyrrolidin-3-ylcarbamate, was obtained as a white solid. LC/MS found [M+H]+=418.4.

Provenance & Evidence