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 → 3-{(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}-imidazolidine-2,4-dione

HRID 215883Notes

Reaction equation

HRID 215883 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([N:16]3[C:20](=[O:21])[CH2:19][NH:18][C:17]3=[O:22])[C@@H:13]([OH:23])[C@H:12]2[OH:24])=[C:4]([NH:25][C@H:26]([CH2:34][OH:35])[CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:3]=1.[N+:36]([C:39]1[N:40]=[CH:41][NH:42][CH:43]=1)([O-:38])=[O:37].C1(C(C2C=CC=CC=2)CNC2N=C(N3C=C([N+]([O-])=O)C=N3)N=C3C=2N=CN3[C@@H]2C[C@H](NC(=O)CO)[C@@H](O)[C@H]2O)C=CC=CC=1>>[OH:23][C@H:13]1[C@@H:12]([OH:24])[C@H:11]([N:8]2[CH:7]=[N:6][C:5]3[C:9]2=[N:10][C:2]([N:42]2[CH:43]=[C:39]([N+:36]([O-:38])=[O:37])[N:40]=[CH:41]2)=[N:3][C:4]=3[NH:25][C@H:26]([CH2:34][OH:35])[CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:15][C@@H:14]1[N:16]1[C:20](=[O:21])[CH2:19][NH:18][C:17]1=[O:22]

Participants

4

Reactant 3

HCID 66630082N-{(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-acetamideHCID 866436793-{(1S,2R,3S,4R)-4-[2-Chloro-6-((S)-1-hydroxymethyl-2-phenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-imidazolidine-2,4-dioneHCID 178526856HCID 178526856, compound

Product 1

HCID 670229593-{(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}-imidazolidine-2,4-dione

Procedure

3-{(1S,2R,3S,4R)-4-[2-Chloro-6-((S)-1-hydroxymethyl-2-phenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-imidazolidine-2,4-dione (Intermediate VB) 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-eda98c5a1a44448196e1624d1e44589f
Source dataset
uspto-grants-2012_06
Patent number
US08193164B2

Reaction notes

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