Hydrochloric Acid → HCID 178453818, compound

Participants

Reaction Steps

4-(tert-Butoxycarbonylamino-{[1-(4-chloro-phenyl)-cyclopropylmethyl]-carbamoyl}-methyl)-cyclohexanecarboxylic acid propyl ester (2-2) (1.77 g, 0.0035 mol, 1 eq) was dissolved in MeOH (20 mL) and THF (6 mL). NaOH (0.42 g, 0.0105 mol, 3 eq) in H2O (2 mL) was added. The reaction mixture was stirred at RT and monitored by TLC and LC/MS. After stirring at RT for 20 hours, the reaction mixture was diluted with H2O. The pH was adjusted to pH=3 with 10% HCl while cooling with ice-H2O bath. The aqueous was extracted with EtOAc (3×60 mL). The combined EtOAc was washed with brine. After drying over Na2SO4 and filtration, the filtrate was concentrated under vacuum to dryness. The crude product was purified on silica gel column, eluted with 2% MeOH/CH2Cl2 to give trans-4-(tert-Butoxycarbonylamino-{[1-(4-chloro-phenyl)-cyclopropylmethyl]-carbamoyl}-methyl)-cyclohexanecarboxylic acid 0.56 g (2-3) (34.4%). 1H NMR (DMSO-d6) data is depicted in FIG. 19.

Provenance & Evidence