(2R,3S,4R,5R)-2-((((((2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-2-((phosphonooxy)methyl)tetrahydrofuran-3-yl)oxy)(hydroxy)phosphoryl)oxy)methyl)-5-(6-amino-9H-purin-9-yl)-4-hydroxytetrahydrofuran-3-yl 2-((tert-butoxycarbonyl) (2-(tert-butyldisulfanyl)ethyl)amino)acetate → (2R,3S,4R,5R)-2-((((((2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-2-((phosphonooxy)methyl)tetrahydrofuran-3-yl)oxy)(hydroxy)phosphoryl)oxy)methyl)-5-(6-amino-9H-purin-9-yl)-4-hydroxytetrahydrofuran-3-yl 2-((2-(tert-butyldisulfanyl)ethyl)amino)acetate

HRID 1482221Notes

Reaction equation

HRID 1482221 reaction equation
C(OC([N:8]([CH2:54][CH2:55][S:56][S:57][C:58]([CH3:61])([CH3:60])[CH3:59])[CH2:9][C:10]([O:12][C@H:13]1[C@@H:17]([OH:18])[C@H:16]([N:19]2[CH:27]=[N:26][C:25]3[C:20]2=[N:21][CH:22]=[N:23][C:24]=3[NH2:28])[O:15][C@@H:14]1[CH2:29][O:30][P:31]([O:34][C@H:35]1[CH2:39][C@H:38]([N:40]2[CH:45]=[CH:44][C:43]([NH2:46])=[N:42][C:41]2=[O:47])[O:37][C@@H:36]1[CH2:48][O:49][P:50]([OH:53])([OH:52])=[O:51])([OH:33])=[O:32])=[O:11])=O)(C)(C)C>C(O)(C(F)(F)F)=O>[C:58]([S:57][S:56][CH2:55][CH2:54][NH:8][CH2:9][C:10]([O:12][C@H:13]1[C@@H:17]([OH:18])[C@H:16]([N:19]2[CH:27]=[N:26][C:25]3[C:20]2=[N:21][CH:22]=[N:23][C:24]=3[NH2:28])[O:15][C@@H:14]1[CH2:29][O:30][P:31]([O:34][C@H:35]1[CH2:39][C@H:38]([N:40]2[CH:45]=[CH:44][C:43]([NH2:46])=[N:42][C:41]2=[O:47])[O:37][C@@H:36]1[CH2:48][O:49][P:50]([OH:53])([OH:52])=[O:51])([OH:33])=[O:32])=[O:11])([CH3:61])([CH3:59])[CH3:60]

Participants

3

Reactant 1

HCID 89668422(2R,3S,4R,5R)-2-((((((2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-2-((phosphonooxy)methyl)tetrahydrofuran-3-yl)oxy)(hydroxy)phosphoryl)oxy)methyl)-5-(6-amino-9H-purin-9-yl)-4-hydroxytetrahydrofuran-3-yl 2-((tert-butoxycarbonyl) (2-(tert-butyldisulfanyl)ethyl)amino)acetate2×

Product 1

HCID 89668394(2R,3S,4R,5R)-2-((((((2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-2-((phosphonooxy)methyl)tetrahydrofuran-3-yl)oxy)(hydroxy)phosphoryl)oxy)methyl)-5-(6-amino-9H-purin-9-yl)-4-hydroxytetrahydrofuran-3-yl 2-((2-(tert-butyldisulfanyl)ethyl)amino)acetateYield 81%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(2R,3S,4R,5R)-2-((((((2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-2-((phosphonooxy)methyl)tetrahydrofuran-3-yl)oxy)(hydroxy)phosphoryl)oxy)methyl)-5-(6-amino-9H-purin-9-yl)-4-hydroxytetrahydrofuran-3-yl 2-((tert-butoxycarbonyl)(2-(tert-butyldisulfanyl)ethyl)amino)acetate (Compound 6h-A, 56.2 mg, 0.060 mmol) was dissolved in TFA (1.0 ml), and the mixture was stirred at room temperature for 5 minutes. The reaction solution was concentrated under reduced pressure, and the residue was then purified by Column chromatography (0.05% aqueous TFA solution:0.05% TFA-acetonitrile solution=85:15=85:15) to afford the title compound (40.6 mg, 81%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe residue was then purified by Column chromatography (0.05% aqueous TFA solution:0.05% TFA-acetonitrile solution=85:15=85:15)

Sources & evidence

ORD record
ord-bd9477c0a09b430cb402634707dfe4c0
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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