Sodium Hydroxide → HCID 58553821, compound

Participants

Reaction Steps

To a solution of methyl 4-{1-[2-tert-butoxy-1-(4-chlorophenyl)-2-oxoethyl]butyl}benzoate (prepared as described in PCT Patent Publication WO 2008/042223 A1 published on 10 Apr. 2008, 20 g, 48 mmol) in MeOH was slowly added NaOH (5.0 N in H2O, 19 mL, 95 mmol) at ambient temperature. Once all the ester starting material was consumed by LC-MS analysis, the mixture was concentrated. The residue was partitioned between EtOAc and 1N HCl (aq). The organic layer was then washed with water then saturated NaCl (aq). The organic layer was then dried over Na2SO4, filtered, then concentrated. The resulting acid was used directly for the following step. 1H NMR (400 MHz, DMSO-d6) δ 12.80 (s, 1H); 7.88 (d, J=8 Hz, 2H); 7.48-7.65 (m, 2H); 7.45-7.74 (m, 3H); 7.15 (s, 1H); 3.87 (d, J=11.6 Hz, 1H); 3.15-3.11 (m, 1H); 1.61-1.70 (m, 1H); 1.06-1.14 (m, 1H); 0.97 (s, 9H); 0.76-0.86 (m, 2H); 0.56 (t, 0.1=7.6 Hz, 3H). LC3 2.54 min. (M-tBu+H)+ 347.

Provenance & Evidence