Benzyloxycarbonyl-L-phenylalanine → Alanine, N-benzyloxycarbonyl-3-phenyl-, cyanomethyl ester, L-

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Reaction Steps

1 gram of Z-L-Phe-OH or Z-D-Phe-OH was dissolved in 2 mL of triethylamine and 2 mL of chloroacetonitrile. The reaction was stirred for two hours at room temperature. The reaction was concentrated under vacuum and the residue taken up in 5 mL ethyl acetate. The ethyl acetate was then washed with 2% Na2CO3 (3x), water (2x), 1 N HCl (2x), water (2x), and 0.5 M or higher saline (1x). The organic phase was dried over MgSO4, and concentrated to dryness. The residue was recrystallized from CH2Cl2 /hexanes. Yield for Z-L-Phe-OCH2CN was 1.0 g (89%). M.P. 53°-55° C. [α]d (c 2, DMF)+6.6°. 1H-NMR (CDCl3) 3.1 (d, 2H, Phe βH), 4.7 (m, 3H, αH and cyanomethyl), 5.1 (s, 2H, CBZ βH), 5.2 (d, 1H, amide), 7.3 (m, 10 H, Phe and CBZ phenyl). Z-D-Phe-OCH2CH, yield 0.88 g (78%). M.P. 53°-54° C. [α]d (c, 2, DMF)-6.1°.

Provenance & Evidence