Hydrochloric Acid → HCID 178496730, compound

HRID 1099471Notes

Reaction equation

C([O:3][C:4](=[O:41])[CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([NH:12][C:13](=[O:40])[CH:14]([CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)[N:15]2[C:19]3[CH:20]=[CH:21][C:22]([F:24])=[CH:23][C:18]=3[N:17]=[C:16]2[C@H:25]([O:32][CH3:33])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:8][CH2:7]1)C.[Li+].[OH-].Cl>C(#N)C>[CH:34]1([CH:14]([N:15]2[C:19]3[CH:20]=[CH:21][C:22]([F:24])=[CH:23][C:18]=3[N:17]=[C:16]2[C@H:25]([O:32][CH3:33])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:13]([NH:12][C@H:9]2[CH2:8][CH2:7][C@H:6]([CH2:5][C:4]([OH:41])=[O:3])[CH2:11][CH2:10]2)=[O:40])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of (trans-4-{2-cyclohexyl-2-[5-fluoro-2-((R)-methoxy-phenyl-methyl)-benzoimidazol-1-yl]-acetylamino}-cyclohexyl)-acetic acid ethyl ester (190 mg, 0.34 mmol, 1.0 equiv) in acetonitrile (3 mL) was added a solution of 1 M LiOH (2 mL) and the reaction mixture heated by microwave irradiation to 110° C. for 30 min. A solution of 1 M HCl (25 mL) was added, the organic solvents removed by evaporation under reduced pressure and the residue extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4 and concentrated by evaporation under reduced pressure yielding 138 mg (76%) of the title compound. MS (ISP): 536.4 [M+H]+.

Workup

customthe organic solvents removed by evaporation under reduced pressure
extractionthe residue extracted with ethyl acetate
washThe organic layer was washed with water
dry with materialdried over Na2SO4
concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record: ord-42495dc82c9e4c638eedddaddafd1b34
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143422B2

Reaction notes

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