Trifluoroacetic acid → HCID 68005741, compound

HRID 1026600Notes

Reaction equation

HRID 1026600 reaction equation
C([CH:5]([C@H:9]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[CH:23]=[CH:22][C:21]([C:24]([N:26]2[CH2:31][CH2:30][CH:29]([N:32]3[C:41]4[C:36](=[N:37][CH:38]=[C:39]([Cl:42])[CH:40]=4)[CH:35]([OH:43])[C:34]([CH2:45][CH2:46][OH:47])([OH:44])[C:33]3=[O:48])[CH2:28][CH2:27]2)=[O:25])=[C:20]([F:49])[CH:19]=1)[CH3:10])[C:6]([OH:8])=[O:7])(C)(C)C.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[Cl:42][C:39]1[CH:40]=[C:41]2[C:36]([CH:35]([OH:43])[C:34]([CH2:45][CH2:46][OH:47])([OH:44])[C:33](=[O:48])[N:32]2[CH:29]2[CH2:30][CH2:31][N:26]([C:24]([C:21]3[CH:22]=[CH:23][C:18]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=4[O:11][C@H:9]([CH3:10])[CH2:5][C:6]([OH:8])=[O:7])=[CH:19][C:20]=3[F:49])=[O:25])[CH2:27][CH2:28]2)=[N:37][CH:38]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 86671391HCID 86671391, compound

Product 1

HCID 68005741HCID 68005741, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane solution (1 ml) of tert-butyl (3R)-3-{[4′-({4-[7-chloro-3-(2-hydroxyethyl)-2-oxo-3,4-dihydroxy-1,5-naphthyridin-1(2H)-yl]piperidin-1-yl}carbonyl)-3′-fluorobiphenyl-2-yl]oxy}butanoic acid (28.3 mg) were added at room temperature triethylsilane (20.2 mg) and trifluoroacetic acid (0.5 ml). The reaction solution was stirred for 6 hours, and then concentrated under reduced pressure. The resulting residue was purified by silica gel thin layer chromatography to afford (3R)-3-{[4′-({4-[7-chloro-3-(2-hydroxyethyl)-2-oxo-3,4-dihydroxy-1,5-naphthyridin-1(2H)-yl]piperidin-1-yl}carbonyl)-3′-fluorobiphenyl-2-yl]oxy}butanoic acid (25.0 mg).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe resulting residue was purified by silica gel thin layer chromatography

Sources & evidence

ORD record
ord-6cfb0a49693f49e1b793cf9be2d23365
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

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