Trifluoroacetic acid → HCID 117735365, compound

HRID 1482359Notes

Reaction equation

HRID 1482359 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:15][C:16]([NH:18][CH2:19][CH2:20][CH2:21][C@@H:22]([NH:67]C(OC(C)(C)C)=O)[C:23]([O:25][C@H:26]1[C@@H:30]([OH:31])[C@H:29]([N:32]2[CH:40]=[N:39][C:38]3[C:33]2=[N:34][CH:35]=[N:36][C:37]=3[NH2:41])[O:28][C@H:27]1[CH2:42][O:43][P:44]([O:47][C@H:48]1[CH2:52][C@H:51]([N:53]2[CH:58]=[CH:57][C:56]([NH2:59])=[N:55][C:54]2=[O:60])[O:50][C@@H:49]1[CH2:61][O:62][P:63]([OH:66])([OH:65])=[O:64])([OH:46])=[O:45])=[O:24])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>ClCCl>[NH2:67][C@H:22]([CH2:21][CH2:20][CH2:19][NH:18][C:16]([O:15][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:17])[C:23]([O:25][C@H:26]1[C@@H:30]([OH:31])[C@H:29]([N:32]2[CH:40]=[N:39][C:38]3[C:33]2=[N:34][CH:35]=[N:36][C:37]=3[NH2:41])[O:28][C@H:27]1[CH2:42][O:43][P:44]([O:47][C@H:48]1[CH2:52][C@H:51]([N:53]2[CH:58]=[CH:57][C:56]([NH2:59])=[N:55][C:54]2=[O:60])[O:50][C@@H:49]1[CH2:61][O:62][P:63]([OH:66])([OH:65])=[O:64])([OH:46])=[O:45])=[O:24]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117736151HCID 117736151, compound

Product 1

HCID 117735365HCID 117735365, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.117 mL) was added to a solution of (2S)-(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 5-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)pentanoate (Compound tk67) (30 mg, 0.030 mmol) in dichloromethane (1.1 mL), and the mixture was stirred at room temperature for 35 minutes. Following concentration under reduced pressure, the resulting residue was purified by reverse-phase silica gel column chromatography (0.05% aqueous trifluoroacetic acid solution/0.05% trifluoroacetic acid-acetonitrile solution) to afford (2S)-(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-amino-5-(((benzyloxy)carbonyl)amino)pentanoate (Orn(Z)-pdCpA) (Compound tk68) (24.4 mg, 91%).

Workup

  1. concentrationconcentration under reduced pressure
  2. customthe resulting residue was purified by reverse-phase silica gel column chromatography (0.05% aqueous trifluoroacetic acid solution/0.05% trifluoroacetic acid-acetonitrile solution)

Sources & evidence

ORD record
ord-1ac2b3e654144447956d2dc9843e92b6
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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