Toluene → HCID 10369153, compound

Participants

Reaction Conditions

Reaction Steps

390 mg (0.853 mmol) of 2,3-dihydro-alpha-methyl-2-oxo-5-phenyl-3-((phenylmethoxy)carbonyl)amino-1H-1,4-benzodiazepine-1-acetic acid was suspended in 28 ml toluene, treated with 1.07 ml (14.6 mmol) thionyl chloride, and stirred at 90° C. for 2 hours. The solvent was removed in vacuo and the residue treated with fresh toluene. The cycle was repeated 4 times. The resulting brown oil was dissolved in 5 ml THF, treated with 185 μl (1.79 mmol) of diethylamine and stirred at room temperature for 1 hour. The solvent was removed in vacuo, treated with 10% Na2CO3 solution and extracted (3x EtOAc). The extracts were combined, washed (1x H2O, 1x brine), dried over Na2SO4, filtered and stripped to dryness in vacuo. Flash chromatography of the crude product on silica gel (10% Et2O in CH2Cl2) gave the title compound which was crystallized from Et2O: m.p. 170°-171° C.

Provenance & Evidence