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benzyl 4-[({[(2-{[(6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purine-2-yl)carbonyl]amino}ethyl)amino]carbonyl}amino)methyl]benzoate → 4-[({[(2-{[(6-[(2,2-diphenylethyl)amino]-9-[(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purin-2-yl)carbonyl]amino}ethyl)amino]carbonyl]-amino)methyl]benzoic Acid

HRID 10432
Notes
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Reaction equation

HRID 10432 reaction equation
[C:1]1([CH:7]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17]([C:19]([NH:21][CH2:22][CH2:23][NH:24][C:25]([NH:27][CH2:28][C:29]3[CH:44]=[CH:43][C:32]([C:33]([O:35]CC4C=CC=CC=4)=[O:34])=[CH:31][CH:30]=3)=[O:26])=[O:20])[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][N:14]3[C@H:45]2[C@H:49]([OH:50])[C@H:48]([OH:51])[C@@H:47]([C:52]([NH:54][CH2:55][CH3:56])=[O:53])[O:46]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)C.[Pd]>[C:57]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17]([C:19]([NH:21][CH2:22][CH2:23][NH:24][C:25]([NH:27][CH2:28][C:29]3[CH:44]=[CH:43][C:32]([C:33]([OH:35])=[O:34])=[CH:31][CH:30]=3)=[O:26])=[O:20])[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][N:14]3[C@H:45]2[C@H:49]([OH:50])[C@H:48]([OH:51])[C@@H:47]([C:52]([NH:54][CH2:55][CH3:56])=[O:53])[O:46]2)[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 60091662benzyl 4-[({[(2-{[(6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purine-2-yl)carbonyl]amino}ethyl)amino]carbonyl}amino)methyl]benzoate

Product 1

HCID 103058904-[({[(2-{[(6-[(2,2-diphenylethyl)amino]-9-[(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purin-2-yl)carbonyl]amino}ethyl)amino]carbonyl]-amino)methyl]benzoic AcidYield 19.2%

Reagents, catalysts & solvents 2

HCID 23938
Palladium
Catalyst
HCID 702EthanolSolvent

Procedure

A solution of benzyl 4-[({[(2-{[(6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purin-2-yl)carbonyl]amino}ethyl)amino]carbonyl}amino)methyl]benzoate (Preparation 55) (150 mg, 0.18 mmol) in ethanol (10 ml) was hydrogenated at room temperature over 10% w/w palladium-on-carbon (30 mg) for 28 hours at 414 KPa. The catalyst was removed by filtration through Arbocel (trade mark) and solvent evaporated under reduced pressure to afford the title compound as a white powder (26 mg).

Workup

  1. customThe catalyst was removed by filtration through Arbocel (trade mark) and solvent
  2. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b3667a2bae3747a0957314fe0b87f185
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07094769B2

Reaction notes

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