Methanol → HCID 59386559, compound

Participants

Reaction Steps

A mixture of (2R,6S,13aS,14aR,16aS,Z)-ethyl 2-(biphenyl-4-yl)-6-(tert-butoxycarbonylamino)-2-methoxy-8-(2-nitrophenylsulfonyl)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[n]pyrrolo[2,1-c][1,4,8]triazacyclopentadecine-14a-carboxylate (60 mg, 0.071 mmol) and LiOH monohydrate (34.0 mg, 1.419 mmol) in tetrahydrofuran (2 mL)/water (0.5 mL)/MeOH (1 mL) was stirred at rt for 18 h. It was then concentrated in vacuo and partitioned between water and ether. The aqueous phase was adjusted to pH=4 using 1N HCl and extracted with EtOAc. The organic phase was then dried over MgSO4, filtered, and concentrated to isolate 52 mg of the crude product as an off-white solid. Purification by preparative HPLC gave 15 mg of (2R,6S,13aS,14aR,16aS,Z)-2-(biphenyl-4-yl)-6-(tert-butoxycarbonylamino)-2-methoxy-8-(2-nitrophenylsulfonyl)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[n]pyrrolo[2,1-c][1,4,8]triazacyclopentadecine-14a-carboxylic acid as a white solid.

Provenance & Evidence