Sodium Hydroxide → HCID 14421500, compound

HRID 1722355Notes

Reaction equation

HRID 1722355 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:20][CH:21]([OH:30])[CH2:22][S:23][CH2:24][CH2:25][C:26]([O:28]C)=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO.O.O>[CH2:1]([O:8][C:9]1[C:14]([CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:20][CH:21]([OH:30])[CH2:22][S:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 14421499HCID 14421499, compound

Product 1

HCID 14421500HCID 14421500, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

0.675 g (1.63 mmol) of methyl 7-(2-benzyloxy-3-cyclopentylphenyl)-6-hydroxy-4-thiaheptanoate (Example 1) is dissolved in 10 ml of methanol/water 9:1, and 0.7 g (17.5 mmol) of NaOH dissolved in a little water is added. The mixture is left to stir at room temperature overnight, then the solvent is removed by distillation in vacuo, and the residue is acidified with cold 1N hydrochloric acid. Three extractions with diethyl ether are carried out, and the organic phases are washed twice with saturated brine and dried over sodium sulfate, and the solvent is removed by distillation in vacuo. 444 mg (66% of theory) of 7-(2-benzyloxy-3-cyclopentylphenyl)-6-hydroxy-4-thiaheptanoic acid are obtained.

Workup

  1. additionis added
  2. waitThe mixture is left
  3. customthe solvent is removed by distillation in vacuo
  4. extractionThree extractions with diethyl ether
  5. washthe organic phases are washed twice with saturated brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvent is removed by distillation in vacuo

Sources & evidence

ORD record
ord-188170b0bdbe4e5386f90cd60a4a2d1f
Source dataset
uspto-grants-1989_08
Patent number
US04855323

Reaction notes

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