(S)-Benzyl 2-amino-3-(4-hydroxyphenyl)propanoate → Epoxysuccinic acid
反応式
[O:1]1[CH:6]([C:7]([OH:9])=[O:8])[CH:2]1[C:3]([OH:5])=[O:4].CC1C=C(C=CC=1)C[K].C(OC(=O)[C@H](CC1C=CC(O)=CC=1)N)C1C=CC=CC=1>ClCCl>[O:1]1[CH:6]([C:7]([OH:9])=[O:8])[CH:2]1[C:3]([OH:5])=[O:4]参加物
4
実験手順
When epoxysuccinic acid mono m-methylbenzyl ester chloride which was prepared from m-methylbenzyl potassium epoxysuccinate (i.e. m-methylbenzyl potassium oxirane 2,3-dicarboxylate) in a manner as described in Example 46 was reacted with L-tyrosine benzyl ester in dichloromethane by the same method as described in Example 47, N-(3-m-methylbenzyloxycarbonyloxirane-2-carbonyl)-L-tyrosine benzyl ester(EP-148) was obtained as a colorless oil. Yield 61%. Mass: m/e 489 (M+). IRνfilm (cm-1): 3480 (amine, hydroxy), 1750 (ester, 1685, 1540 (amide), 897 (epoxide). NMR(CDCl3)δ: 2.30 (3H, s), 3.02 (2H, d, J=6 Hz), 3.21 (0.5H, d, J=2 Hz), 3.47 (0.5H, d, J=2 Hz), 3.60 (0.5H, d, J=2 Hz), 3.64 (0.5H, d, J=2 Hz), 4.75 (1H, m), 5.12 (4H, s), 6.35 (1H, b), 6.25-7.20 (8H, m), 7.30 (5H, s).