Lithium Hydroxide → 4-{[1h-Benzimidazol-2-yl(4-tert-butylcyclohexyl)amino]methyl}benzoic acid

HRID 229983Notes

Reaction equation

[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28]C)=[O:27])=[CH:24][CH:23]=1)[CH:11]1[CH2:16][CH2:15][CH:14]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:13][CH2:12]1.[Li+].[OH-]>O1CCOCC1.O>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=1)[CH:11]1[CH2:16][CH2:15][CH:14]([C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:13][CH2:12]1

Participants

Conditions

Temperature: 40 °C

Procedure

To the title compound of Example 1 Step C (0.21 mmol, 90 mg) in 2 mL of dioxane was added a solution of LiOH (2.1 mmol, 52 mg) in 0.6 mL of H2O. The reaction was stirred at 40° C. for 3 h. The product was partitioned into EtOAc/H2O acidified with 2 N HCl. The aqueous phase was washed with EtOAc and the combined organic phase was dried with MgSO4 and concentrated under reduced pressure affording a yellow solid. HPLC A: 1.98 min.

Workup

customThe product was partitioned into EtOAc/H2O
washThe aqueous phase was washed with EtOAc
dry with materialthe combined organic phase was dried with MgSO4
concentrationconcentrated under reduced pressure
customaffording a yellow solid
custom1.98 min.

Sources & evidence

ORD record: ord-053797de5869425bb0b20c5ab2f8b347
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07563815B2

Reaction notes

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