Hydrochloric Acid → HCID 68837898, compound

HRID 229994Notes

Reaction equation

HRID 229994 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([N:11]([CH2:28][C:29]2[CH:38]=[CH:37][C:32]([C:33]([O:35]C)=[O:34])=[CH:31][CH:30]=2)[C:12]2[N:16]([CH2:17][CH2:18][O:19][Si](C)(C)C)[C:15]3[CH:24]=[CH:25][CH:26]=[CH:27][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]([CH2:28][C:29]2[CH:30]=[CH:31][C:32]([C:33]([OH:35])=[O:34])=[CH:37][CH:38]=2)[C:12]2[N:16]([CH2:17][CH2:18][OH:19])[C:15]3[CH:24]=[CH:25][CH:26]=[CH:27][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 68838381Methyl 4-{[(4-tert-butylcyclohexyl)(1-{2-[(trimethylsilyl)oxy]ethyl}-1H-benz-imidazol-2-yl)amino]methyl}benzoate

Product 1

HCID 68837898HCID 68837898, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

To the title compound of Example 10 Step A (0.13 mmol, 73 mg) in 2 mL of dioxane was added a solution of LiOH (1.25 mmol, 30 mg) in 1 mL of H2O. The resulting solution was stirred at 40° C. overnight. The reaction mixture was taken up in a pH 7 buffer solution and EtOAc. The mixture was acidified with 2 N HCl until two clear layers formed after agitation. The organic layer was collected and the aqueous layer was washed with EtOAc. The combined organic layers were dried with MgSO4 and concentrated under reduced pressure to afford the acid as a beige solid. MS (ESI): m/z 450 (M+H). HPLC A: 2.05 min.

Workup

  1. customformed after agitation
  2. customThe organic layer was collected
  3. washthe aqueous layer was washed with EtOAc
  4. dry with materialThe combined organic layers were dried with MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-44d32c51ee8748bba403130a7731057d
Source dataset
uspto-grants-2009_07
Patent number
US07563815B2

Reaction notes

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