Dimethylformamide → HCID 69939144, compound

Participants

Reaction Steps

To a stirred solution of L-prolin-N-(2-(1-tert-butyloxycarbonylaminoethyl)-5-chlorobenzyl)amide from the previous step (54.6 mg, 0.143 mmol), R-(−)-hexahydromandelic acid(22.62 mg, 0.143 mmol), and NMM (16 μL, 0.143 mmol) in DMF (5 mL) at ambient temperature under nitrogen atmosphere was added BOP reagent (76 mg, 0.172 mmol). The mixture was stirred at ambient temperature for 3 h. The solvent was removed under reduced pressure. The residue was partitioned between EtOAc and saturated aqueous NaHCO3. The EtOAc layer was separated, dried over anhydrous Na2SO4, and filtered. The filtrate solvent was removed under reduced pressure and the residue was purified by preparative thick layer silica gel plate chromatography (2000 μM×20 cm×20 cm) developed with 7.5% MeOH in dichloromethane. Desired bands were removed and eluted with 5% MeOH in dichloromethane which were concentrated in vacuo to obtain 1-((2R)-2-hydroxy-2-cyclohexylethanoyl)-N-(2-(1-(tert-butyloxycarbonylamino)ethyl)-5-chlorobenzyl)-L-prolinamide as a clear colorless oil (40 mg; HPLC RT=3.51 min, method A; LC-MS m/z=522.1).

Provenance & Evidence