Citric Acid → HCID 68006010, compound

HRID 1026587Notes

Reaction equation

HRID 1026587 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][C@H:21]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]1[CH:32]=[C:33]([F:41])[C:34]([C:37]([O:39]C)=[O:38])=[N:35][CH:36]=1)[CH2:22][CH3:23])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[Si:1]([O:18][CH2:19][CH2:20][C@H:21]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]1[CH:32]=[C:33]([F:41])[C:34]([C:37]([OH:39])=[O:38])=[N:35][CH:36]=1)[CH2:22][CH3:23])([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 68006112HCID 68006112, compound

Product 1

HCID 68006010HCID 68006010, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran solution (7.0 ml) of methyl 5-(2-{[(1R)-3-{[tert-butyl(diphenyl)silyl]oxy}-1-ethylpropyl]oxy}phenyl)-3-fluoropyridine-2-carboxylate (440 mg) was added at room temperature 1 N aqueous sodium hydroxide solution (1.69 ml), followed by stirring for 2 hours. The reaction solution was poured into a 10% aqueous citric acid solution, and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford 5-(2-{[(1R)-3-{[tert-butyl(diphenyl)silyl]oxy}-1-ethylpropyl]oxy}phenyl)-3-fluoropyridine-2-carboxylic acid (429 mg).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3e5010f1fbe5442d89f9847335eb8960
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

Loading…