Trifluoroacetic acid → HCID 117736109, compound

HRID 1482327Notes

Reaction equation

HRID 1482327 reaction equation
FC(F)(F)C(O)=O.[N:8]([C:11]1[CH:81]=[CH:80][CH:79]=[CH:78][C:12]=1[CH2:13][O:14][C:15]([NH:17][CH2:18][C@H:19]([S:75][S:76][CH3:77])[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:16])=[N+:9]=[N-:10]>ClCCl>[NH2:67][C@H:22]([CH2:21][CH2:20][C@@H:19]([S:75][S:76][CH3:77])[CH2:18][NH:17][C:15]([O:14][CH2:13][C:12]1[CH:78]=[CH:79][CH:80]=[CH:81][C:11]=1[N:8]=[N+:9]=[N-:10])=[O:16])[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 117735646HCID 117735646, compound

Product 1

HCID 117736109HCID 117736109, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 10% solution of trifluoroacetic acid in dichloromethane (0.1 mL) was added to a solution of (2S,5S)-(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 6-((((2-azidobenzyl)oxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)-5-(methyldisulfanyl)hexanoate (Compound tk17) (2.8 mg, 2.504 μmol) in dichloromethane (0.1 mL), and the mixture was stirred at room temperature for 60 minutes. Following concentrated 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,5S)-(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-6-((((2-azidobenzyl)oxy) carbonyl)amino)-5-(methyldisulfanyl)hexanoate (Lys(5S-SSMe) (oAcbz)-pdCpA) (Compound tk18) (1.4 mg, 55%).

Workup

  1. concentrationFollowing concentrated 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-df6f5c43d7d848879815e0f2c5d1754b
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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