Ethyl isocyanate → HCID 69818230, compound

Participants

Reaction Steps

To a 0.5 M solution of tert-butyl N-[(1S)-1-(4-aminobenzyl)-2-hydroxyethyl]-N-((2S)-2-hydroxy-3-phenoxypropyl)carbamate in dichloroethane (40 μl) were added successively 2.0 M solution of N,O-bis(trimethylsilyl)-acetamide in 1-methyl-2-pyrrolidinone (10 μl), 1.0 M solution of ethyl isocyanate in 1-methyl-2-pyrrolidinone (24 μl), and 0.1 M solution of N-ethyldiisopropylamine in 1-methyl-2-pyrrolidinone (20 μl) at room temperature. After shaking at room temperature for 30 minutes, the solution was treated with 500 μl of trifluoroacetic acid/water (95/5) at 50° C. for 30 minutes. The mixture was evaporated and the residue was purified by reverse phase HPLC (0-100% acetonitrile in water (containing 0.1% trifluoroacetic acid)) to give N-[4-[(2S)-3-hydroxy-2-[[(2S)-2-hydroxy-3-phenoxypropyl]amino]propyl]phenyl]-N′-propylurea trifluoroacetate (5.51 mg) as a pale yellow oil.

Provenance & Evidence