HCID 24862889, compound → HCID 24863555, compound

HRID 1882558Notes

Reaction equation

HRID 1882558 reaction equation
C(OC(=O)[NH:10][C@H:11]1[CH2:15][C@@H:14]([N:16]2[CH:24]=[N:23][C:22]3[C:17]2=[N:18][C:19]([N:40]2[CH2:44][CH2:43][C@@H:42]([NH:45][C:46]([NH:48][CH2:49][C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][N:51]=4)=[O:47])[CH2:41]2)=[N:20][C:21]=3[NH:25][CH2:26][CH:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@H:13]([OH:56])[C@@H:12]1[OH:57])C1C=CC=CC=1>C(O)C.[Pd]>[NH2:10][C@H:11]1[CH2:15][C@@H:14]([N:16]2[CH:24]=[N:23][C:22]3[C:17]2=[N:18][C:19]([N:40]2[CH2:44][CH2:43][C@@H:42]([NH:45][C:46]([NH:48][CH2:49][C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][N:51]=4)=[O:47])[CH2:41]2)=[N:20][C:21]=3[NH:25][CH2:26][CH:27]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C@H:13]([OH:56])[C@@H:12]1[OH:57]

Participants

4

Reactant 1

HCID 24862889HCID 24862889, compound

Product 1

HCID 24863555HCID 24863555, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of ((1S,2R,3S,4R)-4-{6-(2,2-diphenyl-ethylamino)-2-[(R)-3-(3-pyridin-2-ylmethyl-ureido)-pyrrolidin-1-yl]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-carbamic acid benzyl ester (0.13 g, 166 μmol) in ethanol (9 ml) under an inert atmosphere of Argon is treated with Palladium (10% on charcoal) (44 mg). The reaction mixture is placed under an atmosphere of hydrogen and stirred at room temperature overnight and then filtered through Celite™. The filtrate is concentrated in vacuo to afford the title compound. (MH+ 649.89)

Workup

  1. filtrationfiltered through Celite™
  2. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-c4e10e26717c4ba098af112d1b41dded
Source dataset
uspto-grants-2012_11
Patent number
US08318750B2

Reaction notes

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