Hydrochloric Acid → HCID 178453693, compound

Participants

Reaction Steps

cis-/trans-4-(1-tert-Butoxycarbonylamino-2-{[1-(4-chloro-phenyl)-cyclopropane-carbonyl]-amino}-ethyl)-cyclohexanecarboxylic acid propyl ester (1-9) (1.26 g, 0.00248 mol, 1 eq) was dissolved in THF (20 mL) and MeOH (10 mL) in a 250 mL RB flask LiOH (0.12 g, 0.00497 mol, 2 eq) in H2O (5 mL) was added to this solution. The reaction mixture was stirred at RT for 1 hour. NaOH (MW 40, 0.0075 mol, 3 eq) in H2O (5 mL) was added to the above reaction mixture. The reaction mixture was stirred at RT overnight. The reaction mixture was diluted with H2O. The pH was adjusted to 23 with 5% HCl while cooling with an ice-H2O bath. THF and MeOH were removed under vacuum. The residue was extracted with EtOAc (3×80 mL). The combined EtOAc extracts were washed with brine (1×80 mL), dried over Na2SO4 and solvent evaporated to dryness. The crude product was purified on silica gel column, eluting with MeOH/CH2Cl2 (1.25˜10%) to afford 0.28 g plus 0.23 g (less pure) (46% yield) of 1-10. The 1H NMR (DMSO-d6) data is depicted in FIG. 7.

Provenance & Evidence