Lithium Hydroxide → 3-[[[3-(4-Acetyl-3-hydroxy-2-propylphenoxy)-2-hydroxypropyl]thio]methyl]-1-oxa-4-thiaspiro[4.4]nonane-7-acetic acid

HRID 1608281Notes

Reaction equation

HRID 1608281 reaction equation
[C:1]([C:4]1[CH:31]=[CH:30][C:7]([O:8][CH2:9][CH:10]([OH:29])[CH2:11][S:12][CH2:13][CH:14]2[S:18][C:17]3([CH2:22][CH2:21][CH:20]([CH2:23][C:24]([O:26]CC)=[O:25])[CH2:19]3)[O:16][CH2:15]2)=[C:6]([CH2:32][CH2:33][CH3:34])[C:5]=1[OH:35])(=[O:3])[CH3:2].[Li+].[OH-]>C(O)C>[C:1]([C:4]1[CH:31]=[CH:30][C:7]([O:8][CH2:9][CH:10]([OH:29])[CH2:11][S:12][CH2:13][CH:14]2[S:18][C:17]3([CH2:22][CH2:21][CH:20]([CH2:23][C:24]([OH:26])=[O:25])[CH2:19]3)[O:16][CH2:15]2)=[C:6]([CH2:32][CH2:33][CH3:34])[C:5]=1[OH:35])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 19849026Ethyl 3-[[[3-(4-acetyl-3-hydroxy-2-propylphenoxy)-2-hydroxypropyl]thio]methyl]-1-oxa-4-thiaspiro[4.4]nonane-7-acetate

Product 1

HCID 198490283-[[[3-(4-Acetyl-3-hydroxy-2-propylphenoxy)-2-hydroxypropyl]thio]methyl]-1-oxa-4-thiaspiro[4.4]nonane-7-acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product of Example 10 is saponified according to the procedure of Example 2 using 5.3 g (10 mmol) of the above ester and 2M LiOH solution (12.5 ml, 2.5 eq.) in ethanol (50 ml). After stirring overnight at room temperature, the solvent is removed in vacuo and the residue diluted with water. After acidification to pH 2.5 with 0.5N KHSO4, the mixture is extracted with ethyl acetate and dried over magnesium sulfate. The drying agent is filtered and the filtrate is concentrated in vacuo. Further drying of the resultant residue at 60° (0.5 torr) gives the titled compound.

Workup

  1. customthe solvent is removed in vacuo
  2. additionthe residue diluted with water
  3. extractionAfter acidification to pH 2.5 with 0.5N KHSO4, the mixture is extracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe drying agent is filtered
  6. concentrationthe filtrate is concentrated in vacuo
  7. dry with materialFurther drying of the resultant residue at 60° (0.5 torr)

Sources & evidence

ORD record
ord-8fe711a2d08f4f1e8d7a7f70aafeceb0
Source dataset
uspto-grants-1989_09
Patent number
US04870098

Reaction notes

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