Trifluoroacetic acid → HCID 117735886, compound

HRID 1482330Notes

Reaction equation

HRID 1482330 reaction equation
[N:1]([C:4]1[CH:82]=[CH:81][C:7]([CH2:8][O:9][C:10]([NH:12][C@@H:13]([CH2:74][S:75][S:76][C:77]([CH3:80])([CH3:79])[CH3:78])[C:14]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][C@@H:21]([NH:66]C(OC(C)(C)C)=O)[C:22]([O:24][C@H:25]2[C@@H:29]([OH:30])[C@H:28]([N:31]3[CH:39]=[N:38][C:37]4[C:32]3=[N:33][CH:34]=[N:35][C:36]=4[NH2:40])[O:27][C@H:26]2[CH2:41][O:42][P:43]([O:46][C@H:47]2[CH2:51][C@H:50]([N:52]3[CH:57]=[CH:56][C:55]([NH2:58])=[N:54][C:53]3=[O:59])[O:49][C@@H:48]2[CH2:60][O:61][P:62]([OH:65])([OH:64])=[O:63])([OH:45])=[O:44])=[O:23])=[O:15])=[O:11])=[CH:6][CH:5]=1)=[N+:2]=[N-:3].FC(F)(F)C(O)=O>ClCCl>[NH2:66][C@H:21]([CH2:20][CH2:19][CH2:18][CH2:17][NH:16][C:14](=[O:15])[C@@H:13]([NH:12][C:10]([O:9][CH2:8][C:7]1[CH:81]=[CH:82][C:4]([N:1]=[N+:2]=[N-:3])=[CH:5][CH:6]=1)=[O:11])[CH2:74][S:75][S:76][C:77]([CH3:80])([CH3:79])[CH3:78])[C:22]([O:24][C@H:25]1[C@@H:29]([OH:30])[C@H:28]([N:31]2[CH:39]=[N:38][C:37]3[C:32]2=[N:33][CH:34]=[N:35][C:36]=3[NH2:40])[O:27][C@H:26]1[CH2:41][O:42][P:43]([O:46][C@H:47]1[CH2:51][C@H:50]([N:52]2[CH:57]=[CH:56][C:55]([NH2:58])=[N:54][C:53]2=[O:59])[O:49][C@@H:48]1[CH2:60][O:61][P:62]([OH:65])([OH:64])=[O:63])([OH:45])=[O:44])=[O:23]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117735958HCID 117735958, compound

Product 1

HCID 117735886HCID 117735886, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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 6-((R)-2-((((4-azidobenzyl)oxy)carbonyl)amino)-3-(tert-butyldisulfanyl)propanamido)-2-((tert-butoxycarbonyl)amino)hexanoate (Compound tk25) (6.7 mg, 5.44 μmol) in dichloromethane (0.4 mL) was cooled in an ice bath, after which trifluoroacetic acid (0.1 mL) was added and the mixture was stirred at room temperature for 25 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-6-((R)-2-((((4-azidobenzyl)oxy) carbonyl)amino)-3-(tert-butyldisulfanyl)propanamido)hexanoate (Lys(Acbz-Cys(StBu))-pdCpA) (Compound tk26) (1.7 mg, 28%).

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-c6ecbdb2f2a9497c95027bf63d6c3ddb
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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