Sodium Hydroxide → 3-(3-Cyclopropyl-2-pyridin-4-yl-3H-imidazol-4-yl)-2-methyl-propionic acid

HRID 732102Notes

Reaction equation

HRID 732102 reaction equation
C([O:3][C:4](=[O:22])[CH:5]([CH3:21])[CH2:6][C:7]1[N:8]([CH:18]2[CH2:20][CH2:19]2)[C:9]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[N:10][CH:11]=1)C.[OH-].[Na+]>CO>[CH:18]1([N:8]2[C:7]([CH2:6][CH:5]([CH3:21])[C:4]([OH:22])=[O:3])=[CH:11][N:10]=[C:9]2[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 578379853-(3-cyclopropyl-2-pyridin-4-yl-3H-imidazol-4-yl)-2-methyl-propionic acid ethyl ester

Product 1

HCID 578379903-(3-Cyclopropyl-2-pyridin-4-yl-3H-imidazol-4-yl)-2-methyl-propionic acidYield 76.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(3-cyclopropyl-2-pyridin-4-yl-3H-imidazol-4-yl)-2-methyl-propionic acid ethyl ester (1.02 g, 3.40 mmol) was mixed with MeOH (8 ml) and sodium hydroxide (1N in water, 5.1 ml, 5.10 mmol). This mixture was left stirring at r.t. for 5 h, followed by concentration in-vacuo. The isolated residue was treated with aq. HCl (2N, 6 ml) to isolate the title compound (702 mg, 76%). 1H-NMR (DMSO-d6): 8.63 (dd, 2H), 7.74 (dd, 2H), 6.82 (s, 1H), 3.55 (m, 1H), 3.09 (m, 1H), 2.82 (m, 2H), 1.19 (d, 3H), 1.08 (m, 2H), 0.56 (m, 2H).

Workup

  1. waitThis mixture was left
  2. concentrationfollowed by concentration in-vacuo
  3. additionThe isolated residue was treated with aq. HCl (2N, 6 ml)

Sources & evidence

ORD record
ord-e2effea10bbe433ea6023d818120c84e
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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