Hydrochloric Acid → HCID 118308680, compound

HRID 923518Notes

Reaction equation

[CH:1]1([CH2:7][O:8][C:9]2[C:10]3[N:11]([C:15]([C:19]([NH:21][C@@:22]([C:26]4[CH:27]=[C:28]([CH:33]=[CH:34][CH:35]=4)[C:29]([O:31]C)=[O:30])([CH3:25])[CH2:23][OH:24])=[O:20])=[C:16]([CH3:18])[N:17]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CO.[OH-].[Na+].Cl>C1COCC1>[CH:1]1([CH2:7][O:8][C:9]2[C:10]3[N:11]([C:15]([C:19]([NH:21][C@@:22]([C:26]4[CH:27]=[C:28]([CH:33]=[CH:34][CH:35]=4)[C:29]([OH:31])=[O:30])([CH3:25])[CH2:23][OH:24])=[O:20])=[C:16]([CH3:18])[N:17]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 40 °C

Procedure

To a mixture of 86 mg of methyl 3-[(2R)-2-({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)-1-hydroxypropan-2-yl]benzoate, 1.9 ml of methanol, and 1.9 ml of THF was added 0.36 ml of a 1 M aqueous sodium hydroxide solution, followed by stirring at 40° C. for 16 hours. The reaction mixture was left to be cooled to room temperature and 1 M hydrochloric acid was then added thereto, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 52 mg of 3-[(2R)-2-({ [8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)-1-hydroxypropan-2-yl]benzoic acid.

Workup

waitThe reaction mixture was left
temperatureto be cooled to room temperature
extractionfollowed by extraction with chloroform
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
customthe solvent was then evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-cac74671e5d54d4a9e7d6a37528b98d8
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278968B2

Reaction notes

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