Lithium Hydroxide → HCID 178525705, compound

HRID 1596520Notes

Reaction equation

HRID 1596520 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([CH2:12][C:13]2[NH:17][C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[N:14]=2)[CH2:8][CH2:7]1)=[O:5])C.[Li+].[OH-]>C1COCC1>[NH:14]1[C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=[C:13]1[CH2:12][C@@H:9]1[CH2:10][CH2:11][C@H:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 18340691HCID 18340691, compound

Product 1

HCID 178525705HCID 178525705, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

The cis/trans mixture of 4-(1H-benzimidazol-2-ylmethyl)-cyclohexanecarboxylic acid ethyl esters (D) (600 mg, 2.1 mmol) was dissolved in a minimal amount of THF (5 mL) and mixed with concentrated aqueous LiOH (2 mL). The reaction was stirred vigorously and heated at 65° C. for 3 h. After cooling and concentration, the crude material was dissolved in 1:1 water/CH3CN and subjected to preparative reverse-phase HPLC to yield (E) cis-4-(1H-benzimidazol-2-ylmethyl)-cyclohexanecarboxylic acid (200 mg, 37%): 1H NMR (400 MHz, CD3OD) δ 7.77 (m, 2 H), 7.60 (m, 2H), 3.11 (d, 2H), 2.62 (m, 1H), 2.10 (m, 3H), 1.65 (m, 4H), 1.43 (m, 2H); mass spectrum m/z 259 [(M+H)+; calcd for C15H19N2O2: 259].

Workup

  1. temperatureAfter cooling
  2. concentrationconcentration
  3. dissolutionthe crude material was dissolved in 1:1 water/CH3CN

Sources & evidence

ORD record
ord-3ea598892c0d4188b131075875a1c9a7
Source dataset
uspto-grants-2001_09
Patent number
US06291499B1

Reaction notes

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