benzyl 2'-{[(1R)-3-{[tert-butyl(diphenyl)silyl]oxy}-1-methylpropyl]oxy}-3-fluorobiphenyl-4-carboxylate → 2'-{[(1R)-3-{[tert-butyl(diphenyl)silyl]oxy}-1-methylpropyl]oxy}-3-fluorobiphenyl-4-carboxylic acid

HRID 1026564Notes

Reaction equation

HRID 1026564 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:35]=[CH:34][C:33]([C:36]([O:38]CC2C=CC=CC=2)=[O:37])=[C:32]([F:46])[CH:31]=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>[C+4].[OH-].[Pd+2].[OH-].[OH-].[OH-].[OH-].[OH-].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:35]=[CH:34][C:33]([C:36]([OH:38])=[O:37])=[C:32]([F:46])[CH:31]=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:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 68006532benzyl 2'-{[(1R)-3-{[tert-butyl(diphenyl)silyl]oxy}-1-methylpropyl]oxy}-3-fluorobiphenyl-4-carboxylate

Product 1

HCID 680062692'-{[(1R)-3-{[tert-butyl(diphenyl)silyl]oxy}-1-methylpropyl]oxy}-3-fluorobiphenyl-4-carboxylic acidYield 68.5%

Reagents, catalysts & solvents 2

HCID 178420936HCID 178420936, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Under a hydrogen atmosphere, a tetrahydrofuran suspension (45 ml) of benzyl 2′-{[(1R)-3-{[tert-butyl(diphenyl)silyl]oxy}-1-methylpropyl]oxy}-3-fluorobiphenyl-4-carboxylate (2.23 g) and 20% palladium hydroxide carbon (2.23 g) was stirred at room temperature overnight. The reaction solution was filtered through Celite, and washed with methanol, and the filtrate was concentrated under reduced pressure. The residue was dried to afford 2′-{[(1R)-3-{[tert-butyl(diphenyl)silyl]oxy}-1-methylpropyl]oxy}-3-fluorobiphenyl-4-carboxylic acid (1.31 g).

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. washwashed with methanol
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was dried

Sources & evidence

ORD record
ord-24a596d2d9254b65a4a91c643ff4f098
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

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