Methyl Acrylate → HCID 67074477, compound

Participants

Reaction Conditions

Reaction Steps

To 45.6 g (0.12 mol) of {(R)-2-[tert-Butoxycarbonyl-(3-hydroxy-propyl)-amino]-1-methyl-ethyl}-carbamic acid benzyl ester in 300 ml of MeOH was added 5 g of 10% Pd/C and the mixture was stirred under 1 atmosphere (balloon) of hydrogen for 2 h. The mixture was then filtered through Hyflo (washing with MeOH) and reconcentrated to around 150 ml volume. 11.2 ml (0.12 mol) of methyl acrylate was added and the mixture stirred for 16 h after which time the reaction was concentrated to dryness, the residue redissolved in 50 ml CH2Cl2, cooled to 0° C. and rapidly added via cannula a to a cooled (−15° C.) solution of 24.3 g (0.12 mol) of 3-chloro-cinnamoyl chloride and 24 ml (0.17 mol) of triethylamine in 200 ml of CH2Cl2. On completion of the addition the reaction was stirred for a further 15 minutes after which time the reaction was washed with 10% citric acid solution, sat. aq. NaHCO3, dried (Na2SO4) and concentrated. Purification on a SiO2-column (n-heptane/EtOAc 7:3 to 9:1), afforded the titled compound in 64% yield as a colorless gum. MS: 483.3 (MH+, Cl).

Provenance & Evidence