(1S,2R,3S,5R)-3-(di-tert-butoxycarbonylamino)-5-(2,6-dichloro-purin-9-yl)-cyclopentane-1,2-diol → (1R,2S,3R,5S)-3-(2,6-Dichloro-purin-9-yl)-5-(4-ethyl-[1,2,3]triazol-2-yl)-cyclopentane-1,2-diol

HRID 215858Notes

Reaction equation

HRID 215858 reaction equation
C([N:8](C(OC(C)(C)C)=O)[C@H:9]1[CH2:13][C@@H:12]([N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][C:17]([Cl:24])=[N:18][C:19]=3[Cl:23])[C@H:11]([OH:25])[C@@H:10]1[OH:26])(OC(C)(C)C)=O.ClC1N=C2C(N=CN2[C@@H]2C[C@H](N3[N:53]=[C:52]([CH2:54][CH3:55])[CH:51]=[N:50]3)C=C2)=C(Cl)N=1>>[Cl:24][C:17]1[N:16]=[C:15]2[C:20]([N:21]=[CH:22][N:14]2[C@@H:12]2[CH2:13][C@H:9]([N:8]3[N:53]=[C:52]([CH2:54][CH3:55])[CH:51]=[N:50]3)[C@@H:10]([OH:26])[C@H:11]2[OH:25])=[C:19]([Cl:23])[N:18]=1

Participants

3

Reactant 2

HCID 57777515(1S,2R,3S,5R)-3-(di-tert-butoxycarbonylamino)-5-(2,6-dichloro-purin-9-yl)-cyclopentane-1,2-diolHCID 866436722,6-Dichloro-9-[(1R,4S)-4-(4-ethyl-[1,2,3]triazol-2-yl)-cyclopent-2-enyl]-9H-purine

Product 1

HCID 86643673(1R,2S,3R,5S)-3-(2,6-Dichloro-purin-9-yl)-5-(4-ethyl-[1,2,3]triazol-2-yl)-cyclopentane-1,2-diol

Procedure

The titled compound is prepared analogously to (1S,2R,3S,5R)-3-(di-Boc-amino)-5-(2,6-dichloro-purin-9-yl)-cyclopentane-1,2-diol (AA4) by replacing di-Boc-[(1S,4R)-4-(2,6-dichloro-purin-9-yl)-cyclopent-2-enyl]-amine with 2,6-dichloro-9-[(1R,4S)-4-(4-ethyl-[1,2,3]triazol-2-yl)-cyclopent-2-enyl]-9H-purine (Step 1).

Sources & evidence

ORD record
ord-b84562ffcbe54167b4bb020c6f85cd3d
Source dataset
uspto-grants-2012_06
Patent number
US08193164B2

Reaction notes

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