Urea → HCID 91453837, compound

Participants

Reaction Steps

To a solution of tert-butyl N-[(1s)-1-(4-aminobenzyl)-2-hydroxyethyl]-N-[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]-carbamate (0.02 mmol) in NMP (40 ul) was added 2.0 M solution of N,O-bis(trimethylsilyl)acetamide (BSA) in N-methyl-2-pyrrolidinone (NMP) (10 μl, 0.02 mmol) and the mixture was shaken for 30 minutes at room temperature. To the solution, 1.0 M solution of an isocyanate derivative (O═C═N—B) corresponding to an objective urea derivative in NMP (24 μl, 0.024 mmol) and 0.1 M solution of N,N-diisopropylethylamine (DIEA) in NMP (20 μl, 0.002 mmol) were added and the mixture was shaken for 30 minutes at 50° C. After cooling to room temperature, 0.5 ml of 95% trifluoroacetic acid (TFA) in water was added to the solution and shaken for 15 hours. The mixture was concentrated under reduced pressure and purified by HPLC (reverse phase C18, 0-80% 0.1% TFA in acetonitrile/0.1% TFA in water). The fractions containing the desired compound were combined, concentrated and dried under reduced pressure to give the objective urea derivative (9).

Provenance & Evidence