benzyl (2E)-2-(acetylamino)-3-(4-amino-3-ethylphenyl)-2-propenoate → N-acetyl-4-amino-3-ethylphenylalanine

HRID 488637Notes

Reaction equation

HRID 488637 reaction equation
[C:1]([NH:4]/[C:5](=[CH:16]/[C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[C:19]([CH2:24][CH3:25])[CH:18]=1)/[C:6]([O:8]CC1C=CC=CC=1)=[O:7])(=[O:3])[CH3:2]>CO.[Pd]>[C:1]([NH:4][C@H:5]([C:6]([OH:8])=[O:7])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[C:19]([CH2:24][CH3:25])[CH:18]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 11013183benzyl (2E)-2-(acetylamino)-3-(4-amino-3-ethylphenyl)-2-propenoate

Product 1

HCID 69800149N-acetyl-4-amino-3-ethylphenylalanine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl (2E)-2-(acetylamino)-3-(4-amino-3-ethylphenyl)-2-propenoate (5 g) and 10% Pd—C (100 mg) in methanol (50 mL) was stirred under an atmosphere of hydrogen (4 atmospheres) at ambient temperature overnight to provide the titled compound. MS (ESI(+)) m/e 251 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 8.02 (d, 1H), 6.77-6.70 (m, 2H), 6.50 (d, 1H), 4.31-4.21 (m, 1H), 2.84 (dd, 1H), 2.65 (dd, 1H), 2.39 (q, 2H), 1.78 (s, 3H), 1.10 (t, 3H).

Sources & evidence

ORD record
ord-8853f32fddd3420ab68c14a9c10cb472
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

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