1,2-Dichloroethane → HCID 21034201, compound

Participants

Reaction Steps

A solution of [4-(3-Allyloxy-5-fluoro-phenyl)-3-tert-butoxycarbonylamino-2-hydroxy-butyl]-(3-ethyl-benzyl)-carbamic acid benzyl ester (1.84 g, 3.03 mmol) in 20% TFA/DCM (30 mL) is prepared and stirred for 1 hour. The reaction mixture is concentrated in vacuo yielding a white solid (2.12 g). Peptide coupling is performed by preparing a solution of 4-(allyl-propyl-carbamoyl)-butyric acid (0.060 g, 2.82 mmol) in CH2Cl2 to which is added EDC (0.74 g, 3.84 mmol) and HOBT (0.52 g, 3.84 mmol) under N2, with stirring. To this solution is added a solution of TEA (1.43 mL, 10.24 mmol), 1-(3-Allyloxy-5-fluoro-benzyl)-3-[benzyloxycarbonyl-(3-ethyl-benzyl)-amino]-2-hydroxy-propyl-ammonium trifluoro-acetate (1.59 g, 2.56 mmol) dissolved in CH2Cl2 (15 mL). Upon complete reaction the mixture is diluted with EtOAc, washed with NaHCO3 and then 1N HCl. The mixture is then neutralized with NaHCO3, and then 0.5N NaOH, treated with activated charcoal, dried with MgSO4, filtered, concentrated in vacuo, yielding a yellow oil. Purification is achieved via flash chromatography using 75% EtOAc/Hexanes. Calculated mass for C41H52FN3O6+H1: 702.3918. Accurate mass found for C41H52FN3O6+H1: 702.3916.

Provenance & Evidence