Water → HCID 86618247, compound

Participants

Reaction Steps

1M BH3 in THF (0.2 mL, 0.2 mmol) was added dropwise to a solution of 1-(tert-butoxycarbonyl)-4-{[1-(phenylsulfonyl)-1H-indol-4-yl]methyl}piperazine-2-carboxylic acid (0.010 g, 0.020 mmol, Intermediate 51) in THF (0.5 mL) and the mixture was stirred for 2 days at room temperature. TFA (1 mL) and water (0.5 mL) were added and the mixture was stirred overnight. The mixture was evaporated and dissolved in MeOH, filtered and purified by reversed phase preparative HPLC using ACE Prep UV C8 150×30 mm, flow 38 mL/min, gradient time 8.5 min using the eluent system: water/0.1% TFA and CH3CN (31-62% MeCN), fractions collected based on UV-signal (254 nm). The purest fractions were pooled and the acetonitrile was evaporated. Yield: 2.7 mg (22%). Colorless oil. MS (electronspray; [M+H]+) m/z 386.4.

Provenance & Evidence