Hydrochloric Acid → HCID 71522974, compound

HRID 1473813Notes

Reaction equation

HRID 1473813 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][C@@H:15]2[CH2:17][C@@H:16]2[CH:18]2[CH2:23][CH2:22][N:21]([CH2:24][C:25]([F:28])([F:27])[F:26])[CH2:20][CH2:19]2)[CH:9]=[C:8]([F:29])[C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Na+].Cl>CO.CCOC(C)=O>[F:29][C:8]1[CH:9]=[C:10]([O:12][CH2:13][CH2:14][C@@H:15]2[CH2:17][C@@H:16]2[CH:18]2[CH2:23][CH2:22][N:21]([CH2:24][C:25]([F:28])([F:26])[F:27])[CH2:20][CH2:19]2)[CH:11]=[C:2]([F:1])[C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 71522895HCID 71522895, compound

Product 1

HCID 71522974HCID 71522974, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A solution of methyl 2,6-difluoro-4-(2-{(1S,2R)-2-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]cyclopropyl}ethoxy)benzoate (16.0 mg, 0.038 mmol) in MeOH (0.75 mL) was treated with NaOH aqueous solution (0.076 mL, 5 M, 0.38 mmol). It was heated at 60° C. for 4 hours. The mixture was cooled to RT, acidified with 2N HCl, diluted with EtOAc, washed with water, brine, dried with sodium sulfate. The solvent was removed under reduced pressure to yield Example 2. LCMS calc: 407.37; obs: 408.01 (M+1).

Workup

  1. temperatureThe mixture was cooled to RT
  2. washwashed with water, brine
  3. dry with materialdried with sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customto yield Example 2

Sources & evidence

ORD record
ord-7292594d918b468c958de52ef5125999
Source dataset
uspto-grants-2015_04
Patent number
US09018200B2

Reaction notes

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