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 353617Notes

Reaction equation

HRID 353617 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

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 23938PalladiumCatalystHCID 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-purine-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-88405f8ca1ac425b93bf96a97c24e0ec
Source dataset
uspto-grants-2004_06
Patent number
US06753322B2

Reaction notes

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