Triphenylphosphine → (5)-Tert-butyl 3-(3-(chloromethyl)phenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamate

Participants

Reaction Steps

(S)-tert-Butyl 3-(3-(hydroxymethyl)phenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamate (1.0 g, 2.42 mmole) was dissolved in CH2Cl2 (5 ml). Triphenylphosphine (666 mg, 2.54 mmole) was added followed by N-chlorosuccinimide (355 mg, 2.66 mmole). After the vigorous reaction subsided, TLC showed ˜10% of unreacted starting material remained. Added 300 mg more N-chlorosuccinimide. TLC showed that the reaction was complete. The reaction mixture was purified without work-up by flash chromatography. Yield=1.0 g. MS (m/z) 433 [M+H]+.

Provenance & Evidence