4-[3-(2-{[9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purine-2-carbonyl]-amino}-ethyl)-ureido]-piperidine-1-carboxylic acid benzyl ester → 9-((1R,4S)-2,3-Dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purine-2-carboxylic acid [2-(3-piperidin-4-yl-ureido)-ethyl]-amide

HRID 1697020Notes

Reaction equation

HRID 1697020 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18]([NH:20][CH2:21][CH2:22][NH:23][C:24]([C:26]2[N:34]=[C:33]3[C:29]([N:30]=[CH:31][N:32]3[C@@H:35]3[CH2:39][C@H:38]([NH:40][C:41](=[O:44])[CH2:42][CH3:43])[C@@H:37]([OH:45])[C@H:36]3[OH:46])=[C:28]([NH:47][CH2:48][CH:49]([C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)[C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[N:27]=2)=[O:25])=[O:19])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[NH:11]1[CH2:12][CH2:13][CH:14]([NH:17][C:18](=[O:19])[NH:20][CH2:21][CH2:22][NH:23][C:24]([C:26]2[N:34]=[C:33]3[C:29]([N:30]=[CH:31][N:32]3[C@@H:35]3[CH2:39][C@H:38]([NH:40][C:41](=[O:44])[CH2:42][CH3:43])[CH:37]([OH:45])[CH:36]3[OH:46])=[C:28]([NH:47][CH2:48][CH:49]([C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=3)[C:56]3[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=3)[N:27]=2)=[O:25])[CH2:15][CH2:16]1

Participants

4

Reactant 1

HCID 666303744-[3-(2-{[9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purine-2-carbonyl]-amino}-ethyl)-ureido]-piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 672746969-((1R,4S)-2,3-Dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purine-2-carboxylic acid [2-(3-piperidin-4-yl-ureido)-ethyl]-amide

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-[3-(2-{[9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purine-2-carbonyl]-amino}-ethyl)-ureido]-piperidine-1-carboxylic acid benzyl ester (0.145 g, 0.174 mmol) in methanol (1 ml) under an atmosphere of Argon is treated with palladium hydroxide on carbon (0.054 g, 20% w/w carbon). The reaction mixture is placed under an atmosphere of hydrogen and stirred at room temperature for 72 hours and then filtered. The filtrate is concentrated in vacuo to yield the titled compound as a green oil.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-3222ad3740744821b74f5b5231c90c41
Source dataset
uspto-grants-2012_04
Patent number
US08163754B2

Reaction notes

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