Sodium Carbonate → HCID 68284530, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (2S,3R,4R)-4-azido-3-methoxy-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester (440 mg, 1.16 mmol) in methanol (3 mL) was hydrogenated with palladium on carbon 10% (124 mg, 1.16 mmol) overnight. The reaction mixture was filtered over a glass fiber filter, washed with methanol and evaporated in vacuo. The residue was dissolved in THF (2 mL) and a 10% aqueous Na2CO3 (3.09 mL, 1.11 mmol) solution was added. The reaction mixture was cooled at 0° C. then FmocOSu dissolved in THF (7 mL) was added and stirred for 2 h at RT. The reaction mixture was concentrated in vacuo to leave a residue which was dissolved in EtOAc (10 mL) and treated with saturated aq. NH4Cl solution. The mixture was extracted with EtOAc (3×20 mL) and the organic layers were collected, dried over MgSO4, filtered and concentrated. The residue was dissolved in DMF (3 mL) then 3-chloro-2-fluoro benzylamine (267 mg, 1.67 mmol) and HBTU (526 mg, 1.38 mmol), DIPEA (292 μl, 1.67 mmol) were added. The resulting orange solution was stirred overnight at RT. Purification by flash column chromatography on silica gel (c-hexane/EtOAc 3:2) afforded the title compound. MS (UPLC/MS): 624/626 [M+H]+, 668/670 [M+HCOO]−; tR (HPLC conditions f): 2.65 min.

Provenance & Evidence