Water → YM 16638

HRID 1165191Notes

Reaction equation

HRID 1165191 reaction equation
[C:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12][C:13]2[S:17][C:16]([S:18][CH2:19][C:20]([O:22]CC)=[O:21])=[N:15][N:14]=2)=[C:6]([CH2:27][CH2:28][CH3:29])[C:5]=1[OH:30])(=[O:3])[CH3:2].[OH-].[Na+].O>CO>[C:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12][C:13]2[S:17][C:16]([S:18][CH2:19][C:20]([OH:22])=[O:21])=[N:15][N:14]=2)=[C:6]([CH2:27][CH2:28][CH3:29])[C:5]=1[OH:30])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 14723570HCID 14723570, compound

Product 1

HCID 128491YM 16638Yield 77.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a mixture of 4.2 g of ethyl [[5-[[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propyl]thio]-1,3,4-thiadiazol-2-yl]thio]acetate obtained in Example 14 and 30 ml of methanol was added 20 ml of an aqueous solution of 5% sodium hydroxide and the mixture was stirred for 30 minutes. Then, 30 ml of water was added to the reaction mixture and methanol was removed under reduced pressure. The residue thus formed was washed with ethyl acetate, acidified with diluted hydrochloric acid, and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue thus formed was recrystallized from 90% ethanol to provide 3.07 g of [[5-[[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propyl]thio]-1,3,4-thiadiazol-2-yl]thio]acetic acid. The properties of the compound thus obtained were same as those of the compound obtained in Example 21.

Workup

  1. customwas removed under reduced pressure
  2. customThe residue thus formed
  3. washwas washed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue thus formed
  9. customwas recrystallized from 90% ethanol

Sources & evidence

ORD record
ord-e4c54bd971f64dd091a4e18ce0c62e6d
Source dataset
uspto-grants-1990_03
Patent number
US04908368

Reaction notes

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