C1(C[N:8]2[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]2[C:14]([NH:16][C@@H:17]([C:20](OC)=O)[CH2:18][OH:19])=O)C=CC=CC=1>CCO.CO.[Pd]>[CH2:10]1[C@@H:9]2[CH2:14][NH:16][C@H:17]([CH2:18][OH:19])[CH2:20][N:8]2[CH2:13][CH2:12][O:11]1Methyl N-{[(3R)-4-(phenylmethyl)-3-morpholinyl]carbonyl}-D-serinate (D48, 3.72 g, 11.55 mmol) was dissolved in EtOH (50 mL), treated with 10% Pd on C (450 mg) then placed under an atmosphere of hydrogen over the weekend. Left stirring for further 6 hours. Added 10% Pd on C (200 mg) and left under an atmosphere of hydrogen overnight. Catalyst removed by filtration through kieselguhr washed with acid, washing well with EtOH. Solvent removed under reduced pressure to afford a colourless oil. Oil dissolved in dry MeOH (15 mL) and heated at 50° C. overnight. Left heating for a further 3 hours before cooling to R.T. Solvent removed under reduced pressure. Residue triturated with DCM to afford the title compound as an off white solid in 35% yield over the 2 steps.
불러오는 중…
