Cl.[NH2:2][C@H:3]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].C([BH3-])#N.C(O)(=O)C.[CH:24](=O)[CH2:25][CH2:26][CH2:27][CH:28]=O>CO.C(Cl)Cl.O>[C:11]1([C@@H:3]([N:2]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1To a slurry of (R)-tert-butyl 2-amino-2-phenylacetate HCL (Chem-Impex, 0.200 g, 0.821 mmol), MP-cyanoborohydride (2.44 mmol/g; 500 mg) and acetic acid (0.141 mL, 2.462 mmol) in MeOH (2.00 mL) and CH2Cl2 (2 mL) at rt was added glutaraldehyde (0.155 mL, 0.821 mmol) as a 50% solution in water. The reaction was stirred for 30 min., the reaction filtered, washed with MeOH and concentrated. The residue was taken up in CH2Cl2, washed with saturated NaHCO3, dried (Na2SO4) and concentrated to give the title compound. MS (DCI; M+H) m/z=276.
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