Ethanol → HCID 68006259, compound

HRID 1026576Notes

Reaction equation

HRID 1026576 reaction equation
C(O)C.O.[Si:5]([O:22][CH2:23][CH2:24][C@H:25]([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]1[CH:39]=[CH:38][C:37]([C:40]([O:42]C)=[O:41])=[C:36]([Cl:44])[CH:35]=1)[CH3:26])([C:18]([CH3:21])([CH3:20])[CH3:19])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[Na+]>O1CCCC1>[Si:5]([O:22][CH2:23][CH2:24][C@H:25]([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]1[CH:39]=[CH:38][C:37]([C:40]([OH:42])=[O:41])=[C:36]([Cl:44])[CH:35]=1)[CH3:26])([C:18]([CH3:20])([CH3:21])[CH3:19])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 68006371HCID 68006371, compound

Product 1

HCID 68006259HCID 68006259, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution in tetrahydrofuran (5.0 ml), ethanol (5.0 ml) and water (5.0 ml) of methyl 2′-{[(1R)-3-{[tert-butyl(diphenyl)silyl]oxy}-1-methylpropyl]oxy}-3-chlorobiphenyl-4-carboxylate (565 mg) was added 1 N aqueous sodium hydroxide solution (1.48 ml), followed by stirring at 60° C. for 8 hours. After the reaction solution was concentrated under reduced pressure, a 10% aqueous citric acid solution and dichloromethane were added to the residue, and the solution was separated. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford 2′-{[(1R)-3-{[tert-butyl(diphenyl)silyl]oxy}-1-methylpropyl]oxy}-3-chlorobiphenyl-4-carboxylic acid.

Workup

  1. concentrationAfter the reaction solution was concentrated under reduced pressure
  2. additiona 10% aqueous citric acid solution and dichloromethane were added to the residue
  3. customthe solution was separated
  4. washThe organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3ffb767fe4ca4867b9eaebffd886dce3
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

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