Acetic Acid → HCID 86618155, compound

Participants

Reaction Conditions

Reaction Steps

To the solution of (1R,2S,5R)-2-((S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)-5-(tert-butoxycarbonylamino)cyclohexanecarboxamide (2.0 g, 4.21 mmol; see Example 1, Step 5) in MeCN (150 mL) and H2O (205 mL), iodobenzene diacetate (1.357 g, 4.21 mmol) was added. The mixture was stirred at 0° C. for 1 h and then allowed to warm to room temperature in the melting ice bath over 14 h. The mixture was acidified to pH 4 with the addition of acetic acid, and then extracted with diethyl ether (2×60 mL). The aqueous layer was concentrated under reduced pressure to remove acetonitrile. The residual solution was extracted with methylene chloride (2×80 mL) after adjusting the pH to 9-10 using saturated NaHCO3. The methylene chloride layer was dried (Na2SO4) and concentrated in vacuo to give the desired tert-butyl (1R,3R,4S)-3-amino-4-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)cyclohexylcarbamate (1.8 g, 4.03 mmol, 96% yield). LC/MS found [M+H]+=447.

Provenance & Evidence