Diphenylphosphinic acid → Diphenylphosphoryloxymethyl ketone

Participants

Reaction Steps

(2S)-4-(tert-butoxy)-2-({[(5R)-5-isopropyl-3-(1-isoquinolinyl)-4,5-dihydro-5-isoxazolyl]carbonyl}amino)-4-oxobutanoic acid [obtained by coupling reaction of Compound (VIIf) with Asp(O-t-Bu)-OMe and hydrolysis] was reacted according to the same procedure as Preparation 5 to give bromomethyl ketone derivative (tert-butyl (3S)-5-bromo-3-({[(5R)-5-isopropyl-3-(1-isoquinolinyl)-4,5-dihydro-5-isoxazolyl]carbonyl}amino)-4-oxopentanoate). This bromomethyl ketone derivative was reacted with diphenylphosphinic acid in KF/DMF (see Preparation 5) to give diphenylphosphoryloxymethyl ketone derivative, which was then reacted according to the same procedure as Example 2 to give the title compound (Compound of Example 60).

Provenance & Evidence