Lithium Hydroxide → HCID 53816519, compound

HRID 1003883Notes

Reaction equation

HRID 1003883 reaction equation
C[O:2][C:3](=[O:19])[CH2:4][C@@:5]([OH:18])([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[CH:6]([CH3:8])[CH3:7].[OH-].[Li+]>CO.O>[OH:18][C@:5]([CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1)([CH:6]([CH3:7])[CH3:8])[CH2:4][C:3]([OH:19])=[O:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 53666244(S)-3-Hydroxy-3-[2-(4-hydroxy-phenyl)-ethyl]-4-methyl-pentanoic acid methyl ester

Product 1

HCID 53816519HCID 53816519, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The title compound was prepared by dissolving (S)-3-hydroxy-3-[2-(4-hydroxy-phenyl)-ethyl]-4-methyl-pentanoic acid methyl ester (0.57 g, 2.15 mmol) from Example TTTT in MeOH (30 mL). Lithium hydroxide (0.18 g, 4.29 mmol) in water (10 mL) was added and the reaction heated to reflux for 1 hour, 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 extracted with Et2O. The solution was dried (MgSO4) and concentrated to give the title compound (m.p. 137-140° C.).

Workup

  1. customThe title compound was prepared
  2. temperaturethe reaction heated
  3. temperatureto reflux for 1 hour
  4. temperaturecooled
  5. customThe product was partitioned between water and Et2O
  6. customThe aqueous layer was decanted
  7. extractionextracted with Et2O
  8. dry with materialThe solution was dried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-637a6e81307244d3a72e9f43563fbdea
Source dataset
uspto-grants-2000_04
Patent number
US06046355

Reaction notes

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