1,2-Dichloroethane → HCID 57870337, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (3R*,5S*)-3-amino-5{-cyclopropyl-[3-(3-methoxy-propoxy)-4-methyl-benzyl]-carbamoyl}-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester, hydrochloride (110 mg, 0.173 mmol), tert-butyl isocyanate (40 μl, 0.35 mmol), DIPEA (34.2 μl, 0.2 mmol) and 1,2-dichloroethane (2 ml) is shaken for 14 h at 50° C. The mixture is diluted with CH2Cl2 and washed with NaHCO3 solution. The organic layer is dried (Na2SO4) and evaporated. The crude product is stirred with a solution of CH2Cl2/piperidine 4:1 (5 mL) for 1 h, the mixture is evaporated and the residue purified by preparative HPLC (C18 column, 10-100% CH3CN+0.1% TFA/H2O+0.1% TFA, 20 min, flow 20 mL 1 min). The combined pure fractions are treated with K2CO3, CH3CN is removed in vacuo, and the residual aqueous phase is extracted three times with CH2Cl2. The combined organic layers are dried (Na2SO4) and evaporated to afford the title compound as a colorless resin. MS: 475.6 [M+H]+; tR (HPLC, Nucleosil C18; 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 8 min, flow 1.5 ml/min): 5.14 min.

Provenance & Evidence