methyl 3-(4-{[4-{{2-[(benzhydryloxy)carbonyl]phenyl}[(benzyloxy)(oxo)acetyl]amino}-N-(methoxycarbonyl)-L-phenylalanyl]amino}butoxy)-1-hydroxy-2-naphthoate → methyl 3-(4-{[4-[(carboxycarbonyl)(2-carboxyphenyl)amino]-N-(methoxycarbonyl)-L-phenylalanyl]amino}butoxy)-1-hydroxy-2-naphthoate

HRID 488684Notes

Reaction equation

HRID 488684 reaction equation
C([O:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]([C:60](=[O:71])[C:61]([O:63]CC1C=CC=CC=1)=[O:62])[C:24]1[CH:59]=[CH:58][C:27]([CH2:28][C@@H:29]([C:35]([NH:37][CH2:38][CH2:39][CH2:40][CH2:41][O:42][C:43]2[C:44]([C:54]([O:56][CH3:57])=[O:55])=[C:45]([OH:53])[C:46]3[C:51]([CH:52]=2)=[CH:50][CH:49]=[CH:48][CH:47]=3)=[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>O1CCOCC1.[Pd]>[C:61]([C:60]([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:59]=[CH:58][C:27]([CH2:28][C@@H:29]([C:35]([NH:37][CH2:38][CH2:39][CH2:40][CH2:41][O:42][C:43]2[C:44]([C:54]([O:56][CH3:57])=[O:55])=[C:45]([OH:53])[C:46]3[C:51]([CH:52]=2)=[CH:50][CH:49]=[CH:48][CH:47]=3)=[O:36])[NH:30][C:31]([O:33][CH3:34])=[O:32])=[CH:26][CH:25]=1)=[O:71])([OH:63])=[O:62]

Participants

4

Reactant 1

HCID 86585332methyl 3-(4-{[4-{{2-[(benzhydryloxy)carbonyl]phenyl}[(benzyloxy)(oxo)acetyl]amino}-N-(methoxycarbonyl)-L-phenylalanyl]amino}butoxy)-1-hydroxy-2-naphthoate

Product 1

HCID 10190294methyl 3-(4-{[4-[(carboxycarbonyl)(2-carboxyphenyl)amino]-N-(methoxycarbonyl)-L-phenylalanyl]amino}butoxy)-1-hydroxy-2-naphthoateYield 56.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To methyl 3-(4-{[4-{{2-[(benzhydryloxy)carbonyl]phenyl}[(benzyloxy)(oxo)acetyl]amino}-N-(methoxycarbonyl)-L-phenylalanyl]amino}butoxy)-1-hydroxy-2-naphthoate (32 mg, 0.033 mmol) in dioxane (1 mL) under N2 was added 10% Pd—C (5 mg) followed by 60% HClO4 (1 drop). The reaction was stirred under 1 atmosphere of H2 for 4 hours and filtered. The solution was applied to a reverse phase HPLC column and purified by eluting with 0% to 70% gradient of acetonitrile/0.1% aqueous trifluoroacetic acid to provide the titled compound (13 mg, 56%).

Workup

  1. filtrationfiltered
  2. custompurified
  3. washby eluting with 0% to 70% gradient of acetonitrile/0.1% aqueous trifluoroacetic acid

Sources & evidence

ORD record
ord-b341210c119e4c468a4aa5756f13f1d7
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

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