Hydrochloric Acid → HCID 14053145, compound

HRID 1381588Notes

Reaction equation

HRID 1381588 reaction equation
[C:1]([C:4]1[CH:26]=[CH:25][C:7]([CH2:8][S:9][C:10]2[S:14][C:13]([NH:15][CH:16]([CH2:22][CH:23]=O)C(OCC)=O)=[N:12][N:11]=2)=[C:6]([CH2:27][CH2:28][CH3:29])[C:5]=1[OH:30])(=[O:3])[CH3:2].[OH-:31].[Na+].[C:33]([O:36]CC)(=[O:35])C.Cl>CO>[C:1]([C:4]1[CH:26]=[CH:25][C:7]([CH2:8][S:9][C:10]2[S:14][C:13]([NH:15][C:16](=[O:31])[CH2:22][CH2:23][C:33]([OH:36])=[O:35])=[N:12][N:11]=2)=[C:6]([CH2:27][CH2:28][CH3:29])[C:5]=1[OH:30])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium Hydroxide2×HCID 86742720HCID 86742720, compound

Product 1

HCID 14053145HCID 14053145, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 8 ml of 90% methanol was suspended 0.27 g of ethyl [[5-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-1,3,4-thiadiazol-2-yl]amino]-4-oxobutyrate obtained in Example 23. Further 2 ml of a 1N aqueous sodium hydroxide solution was added to the suspension followed by stirring at room temperature for 20 minutes. An aqueous sodium hydroxide solution and ethyl acetate were added to the reaction mixture to fractionate. The aqueous phase was made acidic with a 1N hydrochloric acid and extracted with ethyl acetate. After the extract was dried over anhydrous magnesium sulfate, the solvent was distilled off. The residue was recrystallized from isopropyl alcohol to give 0.11 g of 4-[[5-[(4-acetyl-3- hydroxy-2-propylbenzyl)thio]-1,3,4-thiadiazol-2-yl]amino]-4-oxobutyric acid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialAfter the extract was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off
  4. customThe residue was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-2012475a192d4eb29f1ac7fc71a3499a
Source dataset
uspto-grants-1989_02
Patent number
US04803211

Reaction notes

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