(1S,2R,3S,5R)-3-(di-tert-butoxycarbonylamino)-5-(2,6-dichloro-purin-9-yl)-cyclopentane-1,2-diol → (1S,2R,3S,5R)-3-Amino-5-(2,6-dichloro-purin-9-yl)-cyclopentane-1,2-diol trifluoroacetate

HRID 1696985Notes

Reaction equation

HRID 1696985 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.[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37].N[C@H]1C[C@@H](N2C=NC3C2=NC(Cl)=NC=3N)[C@H](O)[C@@H]1O>>[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37].[NH2:8][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]

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 86622621(1S,2R,3S,5R)-3-Amino-5-(6-amino-2-chloro-purin-9-yl)-cyclopentane-1,2-diol trifluoroacetate

Product 1

HCID 86622627(1S,2R,3S,5R)-3-Amino-5-(2,6-dichloro-purin-9-yl)-cyclopentane-1,2-diol trifluoroacetate

Procedure

The title compound is prepared from (1S,2R,3S,5R)-3-(di-Boc-amino)-5-(2,6-dichloro-purin-9-yl)-cyclopentane-1,2-diol using a procedure analogous to that used to prepare (1S,2R,3S,5R)-3-amino-5-(6-amino-2-chloro-purin-9-yl)-cyclopentane-1,2-diol trifluoroacetate in Example 1. MS (ES+) m/e 304 (MH+).

Sources & evidence

ORD record
ord-f43eed4157e04554a9dbe91e5b624f64
Source dataset
uspto-grants-2012_04
Patent number
US08163754B2

Reaction notes

Loading…