Hydrochloric Acid → HCID 86680204, compound

HRID 2402368Notes

Reaction equation

HRID 2402368 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:14]2[CH2:16][C:15]2([F:18])[F:17])[CH2:9][C:10]([O:12]C)=[O:11])=[CH:4][C:3]=1[NH:19][C:20](=[O:35])[C@H:21]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C@@H:22]([CH3:27])[C:23]([F:26])([F:25])[F:24].O.[OH-].[Li+].Cl>O1CCOCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:14]2[CH2:16][C:15]2([F:17])[F:18])[CH2:9][C:10]([OH:12])=[O:11])=[CH:4][C:3]=1[NH:19][C:20](=[O:35])[CH:21]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C@@H:22]([CH3:27])[C:23]([F:24])([F:25])[F:26]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 86680205HCID 86680205, compound

Product 1

HCID 86680204HCID 86680204, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

115 mg (0.21 mmol) of methyl 3-(4-chloro-3-{[(2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoyl]amino}phenyl)-3-(2,2-difluorocyclopropyl)propanoate (isomer 2; Example 125A) were dissolved in a mixture of 2 ml of dioxane and 1 ml of water, and 27 mg (0.64 mmol) of lithium hydroxide monohydrate were added. The mixture was stirred at RT overnight. The solution was then diluted with water and acidified with 1 N hydrochloric acid (pH about 2). The aqueous phase was extracted three times with dichloromethane. The combined organic phases were dried over magnesium sulphate and concentrated under reduced pressure. This gave 101 mg (90% of theory) of the title compound as a diastereomer mixture in the form of a colourless oil.

Workup

  1. additionwere added
  2. extractionThe aqueous phase was extracted three times with dichloromethane
  3. dry with materialThe combined organic phases were dried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7541f00cef4b479184f9bbc37a41f537
Source dataset
uspto-grants-2014_08
Patent number
US08796335B2

Reaction notes

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