4-Ethylbenzaldehyde → HCID 4385963, compound

HRID 377451Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:16])[C@H:4]([CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)[NH2:5].[CH2:17]([C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1)[CH3:18]>>[CH2:17]([C:19]1[CH:26]=[CH:25][C:22]([CH:23]2[C:8]3[NH:9][C:10]4[C:15]([C:7]=3[CH2:6][CH:4]([C:3]([O:2][CH3:1])=[O:16])[NH:5]2)=[CH:14][CH:13]=[CH:12][CH:11]=4)=[CH:21][CH:20]=1)[CH3:18]

Participants

Reactant 2

HCID 208614-Ethylbenzaldehyde

HCID 77980L-Tryptophan, methyl ester

Product 1

HCID 4385963HCID 4385963, compound

Procedure

The same method but starting from racemic tryptophan methyl ester and 4-ethylbenzaldehyde gave the cis and trans isomer of the title compound. Cis isomer: white solid 1H NMR (CDCl3) δ(ppm): 7.65-7.1 (m, 9H, H aromatic); 5.25 (brs, 1H, H-1); 4(dd, 1H, H-3); 3.9 (s, 3H, CO2CH3); 3.4 (ddd, 1H, H-4); 3.1 (m, 1H, H-4); 2.7 (q, 2H, CH2CH3) 1.4 (t, 3H, CH2CH3). Trans isomer: white solid m.p.: 187° C.

Sources & evidence

ORD record: ord-5dfe5f64f1c746fc8529a53b35eac993
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06025494

Reaction notes

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