Potassium Hydroxide → HCID 15284535, compound

HRID 260745Notes

Reaction equation

HRID 260745 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:7]([CH2:10][CH:11]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([O:14]C)=[O:13])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[OH-].[K+]>C(O)C.O>[CH2:1]([C:5]1[N:6]([CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:7]([CH2:10][CH:11]([CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:12]([OH:14])=[O:13])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 22400442HCID 22400442, compound

Product 1

HCID 15284535HCID 15284535, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of methyl 3-[2-n-butyl-1-benzyl-1H-imidazol- 5yl]-2-benzylpropanoate (0.12 g, 0.31 mmol) in 50% aqueous ethanol (4 mL) containing potassium hydroxide (0.072 g, 1.28 mmol) was stirred at 25° C. for 18 hours. The basic solution was diluted with water (8 mL), and extracted with diethyl ether. The water solution was acidified with aqueous hydrochloric acid solution to pH 4, and the product was extracted into methylene chloride, dried, and concentrated. This crude material was dissolved in acetone and acidified with ethereal hydrochloric acid to give a precipitate. Crystallization from acetone/ether provided 0.07 g of 3-[2-n-butyl-1- benzyl-1H-imidazol-5-yl]-2-benzylpropanoic acid; mp 148°-150° C. (hydrochloride salt).

Workup

  1. extractionextracted with diethyl ether
  2. extractionthe product was extracted into methylene chloride
  3. customdried
  4. concentrationconcentrated
  5. dissolutionThis crude material was dissolved in acetone
  6. customto give a precipitate
  7. customCrystallization from acetone/ether

Sources & evidence

ORD record
ord-8c31ae8587f94c1ab9307a7268d310ab
Source dataset
uspto-grants-1996_06
Patent number
US05530017

Reaction notes

Loading…