2-(4-(2-(3-((Benzyloxycarbonylamino)methyl)phenylamino)-2-oxoethoxy)phenyl)-2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)acetic acid → 2-(4-(2-(3-(Aminomethyl)phenylamino)-2-oxoethoxy)phenyl)-2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)acetic acid

HRID 735675Notes

Reaction equation

HRID 735675 reaction equation
C(OC([NH:11][CH2:12][C:13]1[CH:14]=[C:15]([NH:19][C:20](=[O:59])[CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([CH:29]([NH:33][C:34]3[CH:35]=[C:36]4[C:41](=[CH:42][CH:43]=3)[C:40]([N:44]([C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])=[N:39][CH:38]=[CH:37]4)[C:30]([OH:32])=[O:31])=[CH:25][CH:24]=2)[CH:16]=[CH:17][CH:18]=1)=O)C1C=CC=CC=1>CO.[Pd]>[NH2:11][CH2:12][C:13]1[CH:14]=[C:15]([NH:19][C:20](=[O:59])[CH2:21][O:22][C:23]2[CH:24]=[CH:25][C:26]([CH:29]([NH:33][C:34]3[CH:35]=[C:36]4[C:41](=[CH:42][CH:43]=3)[C:40]([N:44]([C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[C:45]([O:47][C:48]([CH3:49])([CH3:50])[CH3:51])=[O:46])=[N:39][CH:38]=[CH:37]4)[C:30]([OH:32])=[O:31])=[CH:27][CH:28]=2)[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 1

HCID 578426372-(4-(2-(3-((Benzyloxycarbonylamino)methyl)phenylamino)-2-oxoethoxy)phenyl)-2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)acetic acid

Product 1

HCID 578427302-(4-(2-(3-(Aminomethyl)phenylamino)-2-oxoethoxy)phenyl)-2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)acetic acidYield 68%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 66D (152 mg) in 10 mL MeOH, was added 10% Pd/C (ca. 20 mg). The mixture was hydrogenated at 5 psi for 20 min. The reaction mixture was filtered, concentrated and purified by flash chromatography (0 to 25% MeOH in DCM) to give 66E (85 mg, 68%). MS (ESI) m/z 672.4(M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. custompurified by flash chromatography (0 to 25% MeOH in DCM)

Sources & evidence

ORD record
ord-7a77b40c55ea4883b81a1bf10207ab3c
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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