N-{(1S,2R,3S,4R)-4-[6-((S)-1-benzyl-2-hydroxy-ethylamino)-2-chloro-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-2-hydroxy-acetamide → N-{(1S,2R,3S,4R)-2,3-Dihydroxy-4-[6-((S)-1-hydroxymethyl-2-phenyl-ethylamino)-2-(4-nitro-imidazol-1-yl)-purin-9-yl]-cyclopentyl}-2-hydroxy-acetamide

HRID 215879Notes

Reaction equation

HRID 215879 reaction equation
[CH2:1]([C@H:8]([NH:11][C:12]1[N:20]=[C:19](Cl)[N:18]=[C:17]2[C:13]=1[N:14]=[CH:15][N:16]2[C@@H:22]1[CH2:26][C@H:25]([NH:27][C:28](=[O:31])[CH2:29][OH:30])[C@@H:24]([OH:32])[C@H:23]1[OH:33])[CH2:9][OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:34]([C:37]1[N:38]=[CH:39][NH:40][CH:41]=1)([O-:36])=[O:35]>>[OH:32][C@H:24]1[C@@H:23]([OH:33])[C@H:22]([N:16]2[CH:15]=[N:14][C:13]3[C:17]2=[N:18][C:19]([N:40]2[CH:41]=[C:37]([N+:34]([O-:36])=[O:35])[N:38]=[CH:39]2)=[N:20][C:12]=3[NH:11][C@H:8]([CH2:9][OH:10])[CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:26][C@@H:25]1[NH:27][C:28](=[O:31])[CH2:29][OH:30]

Participants

3

Reactant 2

HCID 86632435N-{(1S,2R,3S,4R)-4-[6-((S)-1-benzyl-2-hydroxy-ethylamino)-2-chloro-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-2-hydroxy-acetamideHCID 178526856HCID 178526856, compound

Product 1

HCID 67022940N-{(1S,2R,3S,4R)-2,3-Dihydroxy-4-[6-((S)-1-hydroxymethyl-2-phenyl-ethylamino)-2-(4-nitro-imidazol-1-yl)-purin-9-yl]-cyclopentyl}-2-hydroxy-acetamide

Procedure

The title compound can be prepared from N-{(1S,2R,3S,4R)-4-[6-((S)-1-benzyl-2-hydroxy-ethylamino)-2-chloro-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-2-hydroxy-acetamide (Intermediate GC) and 4-nitro-imidazole, as described for N-{(1S,2R,3S,4R)-4-[6-(2,2-diphenyl-ethylamino)-2-(4-nitro-pyrazol-1-yl)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-2-hydroxy-acetamide (Intermediate QD).

Sources & evidence

ORD record
ord-72877b9721f246e8ae01c62ee1e7fa38
Source dataset
uspto-grants-2012_06
Patent number
US08193164B2

Reaction notes

Loading…