Thionyl Chloride → HCID 57670089, compound

Participants

Reaction Conditions

Reaction Steps

{(S)-1-[(4S,5R)-2-(6-tert-Butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester (12.6 mg, example 125) was diluted with methanol (1.5 mL) and trifluoroacetic acid (0.1 mL). The mixture was stirred at 75-80° C. for 1 h. Thionyl chloride (0.3 mL) was added dropwise and the mixture was stirred at 80° C. for 1 h. The mixture was then concentrated and diluted with methanol (2 mL) and neutralized with 15% solution of sodium hydroxide. Purification of the crude product on a preparative HPLC (reversed phase, eluting with acetonitrile and water) gave the title product as a mixture of diastereomers (5.4 mg). HR-MS (ES, m/z) calculated for C33H40Cl2N5O2 [(M+H)+] 608.2554, observed 608.2554.

Provenance & Evidence