Potassium Hydroxide → Rac-2-[3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1h-1,2,4-triazol-1-yl]propionic acid

HRID 660860Notes

Reaction equation

HRID 660860 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:15][CH2:14]3)[C:11](=[O:16])[N:10]([CH:17]([CH3:23])[C:18]([O:20]CC)=[O:19])[N:9]=2)=[CH:4][CH:3]=1.[OH-].[K+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:15][CH2:14]3)[C:11](=[O:16])[N:10]([CH:17]([CH3:23])[C:18]([OH:20])=[O:19])[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 58012037Ethyl rac-2-[3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1h-1,2,4-triazol-1-yl]propionate

Product 1

HCID 58011743Rac-2-[3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1h-1,2,4-triazol-1-yl]propionic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

630 mg (1.88 mmol) of ethyl rac-2-[3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-propionate from Example 85A are placed in 8 ml methanol, treated with 4 ml 20% aqueous potassium hydroxide and stirred for 2 hours at room temperature. The methanol is removed in vacuo, the aqueous residue acidified with 2 N hydrochloric acid, extracted with dichloromethane, and the organic phase dried over sodium sulphate and evaporated in vacuo. 463 mg (80% of theory) of the target compound are thus obtained.

Workup

  1. customThe methanol is removed in vacuo
  2. extractionextracted with dichloromethane
  3. dry with materialthe organic phase dried over sodium sulphate
  4. customevaporated in vacuo
  5. custom463 mg (80% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-7bcbdc1e11754cc48b46a37cf0f82518
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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