Hydrochloric Acid → HCID 68836173, compound

HRID 230006Notes

Reaction equation

HRID 230006 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([N:11]([CH2:23][C:24]2[CH:33]=[CH:32][C:27]([C:28]([O:30]C)=[O:29])=[CH:26][CH:25]=2)[C:12]2[N:16]([CH3:17])[C:15]3[CH:18]=[CH:19][C:20]([OH:22])=[CH:21][C:14]=3[N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].CCOC(C)=O.Cl>O1CCOCC1.O>[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([N:11]([CH2:23][C:24]2[CH:25]=[CH:26][C:27]([C:28]([OH:30])=[O:29])=[CH:32][CH:33]=2)[C:12]2[N:16]([CH3:17])[C:15]3[CH:18]=[CH:19][C:20]([OH:22])=[CH:21][C:14]=3[N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 68835422Methyl 4-{[(4-tert-butylcyclohexyl)(5-hydroxy-1-methyl-1h-benzimidazol-2-yl)amino]methyl}benzoate

Product 1

HCID 68836173HCID 68836173, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of the title compound of Example 15 Step A (0.09 mmol, 40 mg) in 1 mL of dioxane was added LiOH (1 mmol, 24 mg) in 0.5 mL of H2O. The reaction mixture was stirred at 40° C. for 1 h. The reaction mixture was taken up in dilute pH 7 buffer and EtOAc, and acidified with 2 N HCl until two clear layers formed after agitation. The organic layer was collected and the aqueous layer was washed 2× with EtOAc. The combined organic layers were dried with Na2SO4 and concentrated under reduced pressure to afford the acid as a beige solid. HPLC A: 2.01 min.

Workup

  1. customformed after agitation
  2. customThe organic layer was collected
  3. washthe aqueous layer was washed 2× with EtOAc
  4. dry with materialThe combined organic layers were dried with Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e3d56dcf89724739bf1ae950c2753cea
Source dataset
uspto-grants-2009_07
Patent number
US07563815B2

Reaction notes

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