Hydrochloric Acid → HCID 68006255, compound

HRID 1026585Notes

Reaction equation

HRID 1026585 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][C@H:21]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]1[CH:31]=[C:32]([F:40])[C:33]([C:36]([O:38]C)=[O:37])=[N:34][CH:35]=1)[CH3:22])([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.O.[OH-].[Li+].Cl>O1CCCC1>[Si:1]([O:18][CH2:19][CH2:20][C@H:21]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]1[CH:31]=[C:32]([F:40])[C:33]([C:36]([OH:38])=[O:37])=[N:34][CH:35]=1)[CH3:22])([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 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 68006086HCID 68006086, compound

Product 1

HCID 68006255HCID 68006255, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran solution (96 ml) of methyl 5-(2-{[(1R)-3-{[tert-butyl(diphenyl)silyl]oxy}-1-methylpropyl]oxy}phenyl)-3-fluoropyridine-2-carboxylate (4.79 g) was added at room temperature an aqueous solution (48 ml) of lithium hydroxide monohydrate (192 mg), followed by stirring for 90 minutes. To the reaction solution was added 1 N hydrochloric acid for neutralization, followed by extraction with dichloromethane. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to afford 5-(2-{[(1R)-3-{[tert-butyl(diphenyl)silyl]oxy}-1-methylpropyl]oxy}phenyl)-3-fluoropyridine-2-carboxylic acid (3.27 g).

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9dd0189fc7a648e19e281d618047755d
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

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