HCID 86585329, compound → HCID 10168788, compound

HRID 488675Notes

Reaction equation

HRID 488675 reaction equation
C([O:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]([C:58](=[O:69])[C:59]([O:61]CC1C=CC=CC=1)=[O:60])[C:24]1[CH:57]=[CH:56][C:27]([CH2:28][C@@H:29]([C:35]([NH:37][CH2:38][CH2:39][CH2:40][CH2:41][O:42][C:43]2[CH:52]=[C:51]([O:53][CH3:54])[CH:50]=[C:49]([OH:55])[C:44]=2[C:45]([O:47][CH3:48])=[O:46])=[O:36])[NH:30][C:31]([O:33][CH3:34])=[O:32])=[CH:26][CH:25]=1)=[O:16])(C1C=CC=CC=1)C1C=CC=CC=1>CO.[Pd]>[C:59]([C:58]([N:23]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:15]([OH:16])=[O:14])[C:24]1[CH:57]=[CH:56][C:27]([CH2:28][C@@H:29]([C:35]([NH:37][CH2:38][CH2:39][CH2:40][CH2:41][O:42][C:43]2[CH:52]=[C:51]([O:53][CH3:54])[CH:50]=[C:49]([OH:55])[C:44]=2[C:45]([O:47][CH3:48])=[O:46])=[O:36])[NH:30][C:31]([O:33][CH3:34])=[O:32])=[CH:26][CH:25]=1)=[O:69])([OH:61])=[O:60]

Participants

4

Reactant 1

HCID 86585329HCID 86585329, compound

Product 1

HCID 10168788HCID 10168788, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl 2-(4-{[4-{{2-[(benzhydryloxy)carbonyl]phenyl}[(benzyloxy)(oxo)acetyl]amino}-N-(methoxycarbonyl)-L-phenylalanyl]amino}butoxy)-6-hydroxy-4-methoxybenzoate and 10% Pd—C (0.1 g) in methanol (25 mL) was stirred under an atmosphere of hydrogen at ambient temperature for 16 hours. The mixture was filtered through celite and the filtrate concentrated under reduced pressure to provide the titled compound. MS (ESI(+)) m/e 682 (M+H)+; 1H NMR (500 MHz, DMSO-d6) 10.66, 10.67 (s, s, 1H), 8.03-7.96 (m, 1H), 7.90-7.83 (m, 1H), 7.63-7.15 (m, 8H), 6.07-6.05 (m, 2H), 4.18-4.10 (m, 1H), 3.95-3.89 (m, 2H), 3.73 (s, 3H), 3.43 (s, 3H), 3.15-3.02 (m, 2H), 2.95-2.86 (m, 1H), 2.78-2.68 (m, 1H), 1.68-1.56 (m, 2H), 1.54-1.47 (m, 2H).

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-fc8d1a6971a94e0e8e9ccf857f30a335
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

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