Sodium Hydroxide → HCID 67433611, compound

Participants

Reaction Steps

Phenylmethyl 3-[1-[(4-chlorophenyl)methyl]-2-(1-methylethyl)-4,5,6,7-tetrahydro-1H-benzimidazol-7-yl]propanoate (second isomer from chiral HPLC, 18 mg) was dissolved in Methanol (1.5 mL). 3.3 M aqueous sodium hydroxide solution (0.5 mL) was added and the reaction mixture was left to stir at RT. After stirring for 18 h, LCMS of the reaction mixture demonstrated full consumption of the starting material and the formation of the desired acid product. The reaction mixture was concentrated in vacuo and taken up in acetonitrile/water. The resulting solution was acidified to pH 5-6 and loaded onto a 20 g SCX column. The column was washed with two column volumes of acetonitrile/water and then eluted with 10% ammonia in ethanol. The basic washings were concentrated in vacuo to afford the desired product as the ammonium salt (10.1 mg). LC/MS MH+ 361/363, Rt 1.87 mins (5 min system, TFA modifier).

Provenance & Evidence