Hydrochloric Acid → N-[(Benzyloxy)carbonyl]-L-tyrosyl-D-alanylglycine

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Reaction Steps

To a solution of Z-Tyr-D-Ala-Gly-OMe (27) (4.57 g, 0.01 mol) in MeOH (10 ml) was added 1 N NaOH (20 ml, 0.02 mol) at 0° with stirring. The suspension was stirred for 2 hr at 0° C., diluted with water (80 ml), and neutralized with 1 N HCl (20 ml). The precipitated crystals were collected by suction, washed with water and dried under reduced pressure to give Z-Tyr-D-Ala-Gly.OH (28) (3.59 g, 81.0%), mp 102°-104° C. (AcOEt) (lit.* mp 124° C.); [α]D22 18.0° (C=1.0, DMF), (lit.* [α]D22 16.7° (c=0.54, DMF)); NMR (DMSO-d6)δ: 1.16 (3H, d, J=7 Hz, CH3), 2.60-2.90 (2H, m, CH2), 3.80 (2H, d, J=6 Hx, CH2PhOH), 4.10-4.45 (2H, m, 2CH), 5.02 (2H, s, CH2O), 6.63-7.20 (4H, m, HOPh-), 7.40 (5H, s, ArH), 8.10-8.30 (2H, br, 2 NH), 9.10-9.40 (1H, br, OH). Rf (IV)=0.20.

Provenance & Evidence