Hydrochloric Acid → 2-[3-(3-chloro-4-methyl-2-thienyl)-4-isobutyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetic acid

HRID 660915Notes

Reaction equation

HRID 660915 reaction equation
[Cl:1][C:2]1[C:6]([CH3:7])=[CH:5][S:4][C:3]=1[C:8]1[N:12]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:11](=[O:17])[N:10]([CH2:18][C:19]([O:21]CC)=[O:20])[N:9]=1.[OH-].[K+].Cl>CO>[Cl:1][C:2]1[C:6]([CH3:7])=[CH:5][S:4][C:3]=1[C:8]1[N:12]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:11](=[O:17])[N:10]([CH2:18][C:19]([OH:21])=[O:20])[N:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 58011923Ethyl 2-[3-(3-chloro-4-methyl-2-thienyl)-4-isobutyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetate

Product 1

HCID 580120612-[3-(3-chloro-4-methyl-2-thienyl)-4-isobutyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

700 mg (1.96 mmol) of ethyl 2-[3-(3-chloro-4-methyl-2-thienyl)-4-isobutyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetate from Example 248A are placed in 10 ml methanol and treated with 1 ml of 20% aqueous potassium hydroxide. This is stirred overnight at room temperature, the reaction mixture is then adjusted to pH 6 with 1 N hydrochloric acid and directly purified by preparative HPLC [Method 12]. 555 mg (86% of theory) of the target compound are thus obtained.

Workup

  1. customdirectly purified by preparative HPLC [Method 12]
  2. custom555 mg (86% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-f67d951e5eb44542962d260a4454f4fb
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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