{(R)-1-[9-((3aS,4R,6S,6aR)-2,2-Dimethyl-6-propionylamino-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-carbamic acid benzyl ester → N-{(3aR,4S,6R,6aS)-6-[2-((R)-3-amino-pyrrolidin-1-yl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-yl}-propionamide

HRID 2382364Notes

Reaction equation

HRID 2382364 reaction equation
C(OC(=O)[NH:10][C@@H:11]1[CH2:15][CH2:14][N:13]([C:16]2[N:24]=[C:23]3[C:19]([N:20]=[CH:21][N:22]3[C@H:25]3[C@H:32]4[C@H:28]([O:29][C:30]([CH3:34])([CH3:33])[O:31]4)[C@@H:27]([NH:35][C:36](=[O:39])[CH2:37][CH3:38])[CH2:26]3)=[C:18]([NH:40][CH2:41][CH:42]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[N:17]=2)[CH2:12]1)C1C=CC=CC=1>C(O)C.[OH-].[OH-].[Pd+2]>[NH2:10][C@@H:11]1[CH2:15][CH2:14][N:13]([C:16]2[N:24]=[C:23]3[C:19]([N:20]=[CH:21][N:22]3[C@H:25]3[C@@H:32]4[O:31][C:30]([CH3:34])([CH3:33])[O:29][C@@H:28]4[C@@H:27]([NH:35][C:36](=[O:39])[CH2:37][CH3:38])[CH2:26]3)=[C:18]([NH:40][CH2:41][CH:42]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[N:17]=2)[CH2:12]1

Participants

4

Reactant 1

HCID 66630309{(R)-1-[9-((3aS,4R,6S,6aR)-2,2-Dimethyl-6-propionylamino-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-carbamic acid benzyl ester

Product 1

HCID 66629700N-{(3aR,4S,6R,6aS)-6-[2-((R)-3-amino-pyrrolidin-1-yl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-yl}-propionamide

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of {(R)-1-[9-((3aS,4R,6S,6aR)-2,2-dimethyl-6-propionylamino-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-carbamic acid benzyl ester (0.598 g, 0.79 mmol) in ethanol (7.5 ml) under an inert atmosphere of Argon is added palladium hydroxide on carbon (10 mg). The reaction mixture is purged with Argon and placed under an atmosphere of hydrogen overnight. The mixture is filtered and purified by chromatography on silica eluting with 5% MeOH in DCM to yield the title compound. [MH+ 611].

Workup

  1. customThe reaction mixture is purged with Argon
  2. filtrationThe mixture is filtered
  3. custompurified by chromatography on silica eluting with 5% MeOH in DCM

Sources & evidence

ORD record
ord-eb2671e2e53a4156bc252b536308ac43
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

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