HCID 86585331, compound → HCID 86585330, compound

HRID 488677Notes

Reaction equation

HRID 488677 reaction equation
C([O:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]([C:62](=[O:73])[C:63]([O:65][CH2:66][C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)=[O:64])[C:24]1[CH:61]=[CH:60][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:44]=[C:45]([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[CH:46]=[C:47]([OH:53])[C:48]=2[C:49]([O:51][CH3:52])=[O:50])=[O:36])[NH:30][C:31]([O:33][CH3:34])=[O:32])=[CH:26][CH:25]=1)=O)(C1C=CC=CC=1)C1C=CC=CC=1>CO.[Pd]>[C:15](=[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]1[N:23]([C:62](=[O:73])[C:63]([O:65][CH2:66][C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)=[O:64])[C:24]1[CH:25]=[CH:26][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:44]=[C:45]([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[CH:46]=[C:47]([OH:53])[C:48]=2[C:49]([O:51][CH3:52])=[O:50])=[O:36])[NH:30][C:31]([O:33][CH3:34])=[O:32])=[CH:60][CH:61]=1)=[O:14]

Participants

4

Reactant 1

HCID 86585331HCID 86585331, compound

Product 1

HCID 86585330HCID 86585330, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of methyl 3-(4-{[4-{{2-[(benzhydryloxy)carbonyl]phenyl}[(benzyloxy)(oxo)acetyl]amino}-N-(methoxycarbonyl)-L-phenylalanyl]amino}butoxy)-5-hydroxy-1,1′-biphenyl-4-carboxylate (120 mg, 0.12 mM) in methanol (25 mL) was stirred for 16 hours over 10% Pd/C under an atmosphere of H2. The mixture was filtered, concentrated under reduced pressure and purified by preparative HPLC to give the desired product. MS (ESI(+)) m/e 728 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 10.15 (bs, 1H), 8.13-8.06 (m, 1H), 7.99-7.06 (m, 1H), 7.73-7.12 (m, 13H), 6.99-6.89 (m, 2H), 6.74-6.71 (m, 2H), 4.13-4.08 (m, 1H), 4.06-4.02 (m, 2H), 3.75 (s, 3H), 3.43 and 3.42 (2s, 3H total), 3.12-3.06 (m, 2H), 2.89-2.83 (m, 1H), 2.76-2.65 (m, 1H), 1.64-1.58 (m, 2H), 1.53-1.47 (m, 2H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-ec83bd47015845a7aeee042d586f8d07
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

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