Dichloromethane → HCID 72484853, compound

Participants

Reaction Steps

1-Boc-4-(2-[1,2,4]triazol-1-ylmethyl-phenyl)-piperazine was deprotected and coupled to Boc-D-p-Cl-Phe-OH in a manner similar to coupling procedure 1. The coupled product was deprotected and prepared as the chloride salt. To a solution of the chloride salt (1.16 g, 2.52 mmol), 6-hydroxy-1,1-dimethyl-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid (714 mg), DIEA (1.75 mL), HOBt (408 mg), and DMAP (62 mg) in 2.52 mL of CH2Cl2 was added EDC (579 mg). After stirring overnight, the mixture was extracted with EtOAc, washed with water, saturated bicarbonate and brine, and then dried over Na2SO4, filtered and evaporated to dryness. The mixture was chromatographed with 5% MeOH/EtOAc. The diastereomers were separated on a waters symmetry C18 column 80:20 to 50:50 water (0.05% TFA) acetonitrile over 40 minutes detecting at 230 nm. LRMS (ESI+): 628.3 (M+1).

Provenance & Evidence