Ethyl 2-(3-(4-aminobenzyl)ureido)-3-(3-(benzyloxy)phenyl)propanoate → Ethyl 2-(3-(4-aminobenzyl)ureido)-3-(3-hydroxyphenyl)propanoate

HRID 2403241Notes

Reaction equation

HRID 2403241 reaction equation
[NH2:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][NH:7][C:8](=[O:31])[NH:9][CH:10]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23]CC3C=CC=CC=3)[CH:18]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1>CO.[Pd]>[NH2:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][NH:7][C:8](=[O:31])[NH:9][CH:10]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 67255521Ethyl 2-(3-(4-aminobenzyl)ureido)-3-(3-(benzyloxy)phenyl)propanoate

Product 1

HCID 67256084Ethyl 2-(3-(4-aminobenzyl)ureido)-3-(3-hydroxyphenyl)propanoateYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 162 (205 mg) in MeOH (20 ml) was stirred for 1 h under hydrogen atmosphere in the presence of 10% Pd/C. The resulting mixture was filtered through celite and the filtrate was evaporated under reduced pressure to give 163 as white solid (160 mg, 98%). 1H NMR (DMSO): δ 1.28 (t, 3H, J=6.4 Hz), 2.97 (m, 2H), 4.12 (m, 2H), 4.19 (q, 2H, J=6.4 Hz), 4.51 (m, 1H), 5.02 (s, 2H), 6.24 (d, 1H, J=8.3 Hz), 6.46 (m, 1H), 6.63 (d, 2H, J=7.5 Hz), 6.71 (s, 2H), 6.75 (d, 1H, J=7.5 Hz), 7.00 (d, 2H, J=7.5 Hz), 7.19 (t, 1H, J=7.5 Hz), 9.42 (s, 1H). HPLC method B tr=17.75 nm (96.3%). ESI-MS m/z: 358.2 [M+H]+.

Workup

  1. filtrationThe resulting mixture was filtered through celite
  2. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7c77315edc8f48398cbf79f1889848a3
Source dataset
uspto-grants-2014_08
Patent number
US08802666B2

Reaction notes

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