Lithium Hydroxide → 3-[2-(4-Benzyloxy-phenyl)-ethyl]-3-hydroxy-4-methyl-pentanoic acid

HRID 356525Notes

Reaction equation

HRID 356525 reaction equation
C([O:5][C:6](=[O:29])[CH2:7][C:8]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:17][CH:16]=1)([OH:12])[CH:9]([CH3:11])[CH3:10])(C)(C)C.[OH-].[Li+]>CO.O>[CH2:22]([O:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][CH2:13][C:8]([OH:12])([CH:9]([CH3:10])[CH3:11])[CH2:7][C:6]([OH:29])=[O:5])=[CH:16][CH:17]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 539460993-[2-(4-Benzyloxy-phenyl)ethyl]-3-hydroxy-4-methyl-pentanoic acid tert-butyl ester

Product 1

HCID 187986573-[2-(4-Benzyloxy-phenyl)-ethyl]-3-hydroxy-4-methyl-pentanoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The title compound was prepared by dissolving 3-[2-(4-benzyloxy-phenyl)ethyl]-3-hydroxy-4-methyl-pentanoic acid tert-butyl ester (28 g, 70.3 mmol) from Example QQQQ in MeOH (150 mL). Lithium hydroxide (5.9 g, 140.6 mmol) in water (50 mL) was added and the reaction heated to reflux for 5 hours, cooled and pumped to dryness under vacuum. The product was partitioned between water and Et2O. The aqueous layer was decanted, acidified with 1N HCL, and the precipitate was filtered and dried under vacuum to give the title compound (mp 97°-98° C.).

Workup

  1. customThe title compound was prepared
  2. temperaturethe reaction heated
  3. temperatureto reflux for 5 hours
  4. temperaturecooled
  5. customThe product was partitioned between water and Et2O
  6. customThe aqueous layer was decanted
  7. filtrationthe precipitate was filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-6c5cb917f19f45ab887763eebd0bd852
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

Loading…