Benzyl 3-(3-(benzyloxy)phenyl)-2-(3-(4-(tert-butoxycarbonylamino)benzyl)ureido)propanoate → 2-(3-(4-(Tert-butoxycarbonylamino)benzyl)ureido)-3-(3-hydroxyphenyl) propanoic acid

HRID 1397876Notes

Reaction equation

HRID 1397876 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH:16]([NH:27][C:28]([NH:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[CH:34][CH:33]=2)=[O:29])[C:17]([O:19]CC2C=CC=CC=2)=[O:18])[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[C:42]([O:41][C:39]([NH:38][C:35]1[CH:34]=[CH:33][C:32]([CH2:31][NH:30][C:28](=[O:29])[NH:27][CH:16]([CH2:15][C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([OH:8])[CH:10]=2)[C:17]([OH:19])=[O:18])=[CH:37][CH:36]=1)=[O:40])([CH3:45])([CH3:43])[CH3:44]

Participants

4

Reactant 1

HCID 68334584Benzyl 3-(3-(benzyloxy)phenyl)-2-(3-(4-(tert-butoxycarbonylamino)benzyl)ureido)propanoate

Product 1

HCID 683345852-(3-(4-(Tert-butoxycarbonylamino)benzyl)ureido)-3-(3-hydroxyphenyl) propanoic acidYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 174 (410 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 175 as white solid (280 mg, 97%). 1H NMR (DMSO): δ 1.61 (s, 9H), 2.93 (m, 1H), 3.05 (m, 1H), 4.23 (m, 2H), 4.38 (m, 1H), 6.17 (d, 1H, J=8.0 Hz), 6.66 (t, 1H, J=5.9 Hz), 7.16 (t, 1H, J=7.3 Hz), 7.22 (d, 2H, J=7.6 Hz), 7.50 (d, 2H, J=7.6 Hz), 9.38 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-1730da932f9b4f44afa0dd57de651eba
Source dataset
uspto-grants-2014_12
Patent number
US08901295B2

Reaction notes

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