Methanol → HCID 59386557, compound

Participants

Reaction Steps

A mixture of (2S,4R)-methyl 4-(biphenyl-4-yl)-1-((S)-2-(tert-butoxycarbonylamino)-3-(2-nitro-N-(pent-4-enyl)phenylsulfonamido)propanoyl)-4-methoxypyrrolidine-2-carboxylate (185 mg, 0.246 mmol) and LiOH monohydrate (118 mg, 4.93 mmol) in tetrahydrofuran (2 mL)/MeOH (0.5 mL)/Water (1 mL) was stirred at rt for 18 h. The reaction mixture was then concentrated in vacuo and diluted with 5 mL of water. It was then washed with ether. The aqueous phase was adjusted to pH=4 using 1N HCl. It was then extracted with EtOAc, dried over MgSO4, filtered and concentrated in vacuo to yield 160 mg (87%) of (2S,4R)-4-(biphenyl-4-yl)-1-((S)-2-(tert-butoxycarbonylamino)-3-(2-nitro-N-(pent-4-enyl)phenylsulfonamido)propanoyl)-4-methoxypyrrolidine-2-carboxylic acid as a white solid.

Provenance & Evidence