{3-[9-[(1R,2S,3R,4S)-2,3-Dihydroxy-4-(2-hydroxy-acetylamino)-cyclopentyl]-6-((S)-1-hydroxymethyl-2-phenyl-ethylamino)-9H-purin-2-yl]-prop-2-ynyl}-carbamic acid tert-butyl ester → N-{(1S,2R,3S,4R)-4-[2-(3-Amino-prop-1-ynyl)-6-((S)-1-hydroxymethyl-2-phenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-2-hydroxy-acetamide

HRID 215889Notes

Reaction equation

HRID 215889 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]#[C:10][C:11]1[N:19]=[C:18]2[C:14]([N:15]=[CH:16][N:17]2[C@@H:20]2[CH2:24][C@H:23]([NH:25][C:26](=[O:29])[CH2:27][OH:28])[C@@H:22]([OH:30])[C@H:21]2[OH:31])=[C:13]([NH:32][C@H:33]([CH2:41][OH:42])[CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:12]=1)(C)(C)C>Cl.CO>[NH2:7][CH2:8][C:9]#[C:10][C:11]1[N:19]=[C:18]2[C:14]([N:15]=[CH:16][N:17]2[C@@H:20]2[CH2:24][C@H:23]([NH:25][C:26](=[O:29])[CH2:27][OH:28])[C@@H:22]([OH:30])[C@H:21]2[OH:31])=[C:13]([NH:32][C@H:33]([CH2:41][OH:42])[CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[N:12]=1

Participants

4

Reactant 1

HCID 67022958{3-[9-[(1R,2S,3R,4S)-2,3-Dihydroxy-4-(2-hydroxy-acetylamino)-cyclopentyl]-6-((S)-1-hydroxymethyl-2-phenyl-ethylamino)-9H-purin-2-yl]-prop-2-ynyl}-carbamic acid tert-butyl ester

Product 1

HCID 67022977N-{(1S,2R,3S,4R)-4-[2-(3-Amino-prop-1-ynyl)-6-((S)-1-hydroxymethyl-2-phenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-2-hydroxy-acetamide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

{3-[9-[(1R,2S,3R,4S)-2,3-Dihydroxy-4-(2-hydroxy-acetylamino)-cyclopentyl]-6-((S)-1-hydroxymethyl-2-phenyl-ethylamino)-9H-purin-2-yl]-prop-2-ynyl}-carbamic acid tert-butyl ester (Intermediate XA) is dissolved in 1.25 M HCl in MeOH. After stirring at RT for 3 days, the solvent is removed in vacuo to yield the title compound. This is used in the next step without further purification.

Workup

  1. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-b903bfac3b924d269bf175cfeb10cfba
Source dataset
uspto-grants-2012_06
Patent number
US08193164B2

Reaction notes

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