5-ethyl-1H-1,2,3,4-tetrazole → (1R,2S,3R,5S)-3-(2,6-Dichloro-purin-9-yl)-5-(5-ethyl-tetrazol-2-yl)-cyclopentane-1,2-diol

HRID 215859Notes

Reaction equation

HRID 215859 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.[CH2:34]([C:36]1[N:37]=[N:38]N[N:40]=1)[CH3:35]>>[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:38]=[N:37][C:36]([CH2:34][CH3:35])=[N:40]3)[C@@H:10]([OH:26])[C@H:11]2[OH:25])=[C:19]([Cl:23])[N:18]=1

Participants

3

Reactant 2

HCID 2234645-ethyl-1H-1,2,3,4-tetrazoleHCID 57777515(1S,2R,3S,5R)-3-(di-tert-butoxycarbonylamino)-5-(2,6-dichloro-purin-9-yl)-cyclopentane-1,2-diol

Product 1

HCID 59418853(1R,2S,3R,5S)-3-(2,6-Dichloro-purin-9-yl)-5-(5-ethyl-tetrazol-2-yl)-cyclopentane-1,2-diol

Procedure

This compound is prepared analogously to (1S,2R,3S,5R)-3-(di-Boc-amino)-5-(2,6-dichloro-purin-9-yl)-cyclopentane-1,2-diol (Step AA4) by replacing di-t-butyliminodicarboxylate (Step AA3) with 5-ethyl-2H-tetrazole.

Sources & evidence

ORD record
ord-79bccc8cae16482c94bb59deeec5ac31
Source dataset
uspto-grants-2012_06
Patent number
US08193164B2

Reaction notes

Loading…