Dimethylformamide → HCID 11963228, compound

Participants

Reaction Steps

Tert-butyl 3-hydroxy-4-(3-methoxybenzylamino)-1-phenylbutan-2-ylcarbamate was obtained in a single step by the ring opening reaction of tert-butyl-(1-oxiranyl-2-phenylethyl)-carbamate with 3-methoxybenzylamine under reflux condition in 2-propanol. Deprotection of Boc group by treatment of TFA in CH2Cl2 or methanolic HCl provided 3-amino-1-(3-methoxybenzylamino)-4-phenylbutan-2-ol, which was directly exposed to peptide coupling reaction with 3-(N-methylmethylsulfonamido)-5-(1-phenylethylcarbamoyl)benzoic acid in presence of N-ethyl-N′-(dimethylaminopropyl)carbodiimde hydrochloride (EDC), 1-hydroxybenzotriazole hydrate and diisopropylethylamine in a mixture of DMF and CH2Cl2 to afford N1-(3-hydroxy-4-(3-methoxybenzylamino)-1-phenylbutan-2-yl)-5-(N-methylmethylsulfonamido)-N3-(1-phenylethyl)isophthalamide.

Provenance & Evidence