Hydrochloric Acid → HCID 14839461, compound

HRID 1646518Notes

Reaction equation

HRID 1646518 reaction equation
[C:1]([C:4]1[CH:27]=[CH:26][C:7]([CH2:8][S:9][C:10]2[S:14][C:13]([S:15][CH2:16][CH2:17][CH2:18][S:19][CH2:20][C:21]([O:23]CC)=[O:22])=[N:12][N:11]=2)=[C:6]([CH2:28][CH2:29][CH3:30])[C:5]=1[OH:31])(=[O:3])[CH3:2].[OH-].[Na+].C(OCC)(=O)C.Cl>CO>[C:1]([C:4]1[CH:27]=[CH:26][C:7]([CH2:8][S:9][C:10]2[S:14][C:13]([S:15][CH2:16][CH2:17][CH2:18][S:19][CH2:20][C:21]([OH:23])=[O:22])=[N:12][N:11]=2)=[C:6]([CH2:28][CH2:29][CH3:30])[C:5]=1[OH:31])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium Hydroxide2×HCID 14839460HCID 14839460, compound

Product 1

HCID 14839461HCID 14839461, compoundYield 105.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 2 ml of 90% methanol was suspended 0.14 g of ethyl [[3-[[5-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-1,3,4-thiadiazol-2-yl]thio]propyl]thio]acetate obtained in Example 25. Further 1 ml of a 1N aqueous sodium hydroxide solution was added to the suspension followed by stirring at room temperature for 45 minutes. An aqueous sodium hydroxide solution and ethyl acetate were added to the reaction mixture to fractionate. The aqueous phase was made acidic with 1N hydrochloric acid and extracted with ethyl acetate. After the extract was washed with water and then dried over anhydrous magnesium sulfate, the solvent was distilled off. The residue was applied to silica gel column chromatography. Elution with a solvent mixture of hexane-ethyl acetate (1:2) gave 0.14 g of oily [[3-[[5-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-1,3,4-thiadiazol -2-yl]thio]propyl]thio]acetic acid.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter the extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. washElution
  6. additionwith a solvent mixture of hexane-ethyl acetate (1:2)

Sources & evidence

ORD record
ord-edf4ca71d497425b81ea002d0bfe82e3
Source dataset
uspto-grants-1993_01
Patent number
US05180730

Reaction notes

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