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

HRID 1696978Notes

Reaction equation

HRID 1696978 reaction equation
COC1C=CC(C([NH:18][C:19]2[N:27]=[C:26]([Cl:28])[N:25]=[C:24]3[C:20]=2[N:21]=[CH:22][N:23]3[C@@H:29]2[CH2:33][C@H:32]([N:34](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)[C@@H:31]([OH:49])[C@H:30]2[OH:50])C2C=CC(OC)=CC=2)=CC=1.[C:51]([OH:57])([C:53]([F:56])([F:55])[F:54])=[O:52]>ClCCl>[F:54][C:53]([F:56])([F:55])[C:51]([OH:57])=[O:52].[NH2:34][C@H:32]1[CH2:33][C@@H:29]([N:23]2[CH:22]=[N:21][C:20]3[C:24]2=[N:25][C:26]([Cl:28])=[N:27][C:19]=3[NH2:18])[C@H:30]([OH:50])[C@@H:31]1[OH:49]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86622623(1R,2S,3R,5S)-3-(6-{[Bis-(4-methoxy-phenyl)-methyl]-amino}-2-chloro-purin-9-yl)-5-(di-Boc-amino)-cyclopentane-1,2-diol

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1R,2S,3R,5S)-3-(6-{[Bis-(4-methoxy-phenyl)-methyl]-amino}-2-chloro-purin-9-yl)-5-(di-Boc-amino)-cyclopentane-1,2-diol (600 mg, 0.84 mmol) is dissolved in dichloromethane (4 ml). TFA (2 ml) is added and the reaction mixture is stirred at room temperature. The reaction is shown to be complete by LCMS after 18 hours. The solvent is removed in vacuo and the title compound is obtained after purification by reverse phase column chromatography (Isolute™ C18, 0-100% acetonitrile in water—0.1% TFA). 1H nmr (MeOD, 400 MHz); 8.10(s, 1H), 4.80(m, 1H), 4.60(m, 1H), 4.30(m, 1H), 3.60(m, 1H), 2.85(m, 1H), 2.30(m, 1H). MS (ES+) m/e 285 (MH+).

Workup

  1. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-77e93398d2aa408dbb79ff1708984b8a
Source dataset
uspto-grants-2012_04
Patent number
US08163754B2

Reaction notes

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