Morpholine → HCID 70225157, compound

Participants

Reaction Steps

A mixture of 33.4 mg (0.050 mmol) of [3-[2-[benzyloxycarbonyl-[4-[4-(methanesulfonylamino)phenyl]butyl]amino]-ethyl]-2-(3,5-dimethylphenyl)-1H-indole-5-carboxylic acid, 26.0 mg (0.050 mmol) of PyBOP reagent, 0.010 mL (7.3 mg, 0.072 mmol) of triethylamine, 0.0065 mL (6.5 mg, 0.075 mmol) of morpholine, and 0.0400 mL of dry methylene chloride was stirred under nitrogen at room temperature in a stoppered flask. After 5.5 hours, the solution was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic phase was dried over sodium sulfate, filtered, and concentrated in vacuo. Purification of the crude product by preparative tlc on 2 1000-micron silica gel GF plates (developed in 93:7 CH2Cl2) afforded a quantitative yield amorphous, white solid; homogeneous by TLC in 95:5 CH2Cl2-MeOH. 500 MHz 1H NMR (CDCl3) was complex, owing to rotamers, but was consistent with the assigned structure. Mass spectrum (ESI): m/e=737.2 (M+H).

Provenance & Evidence