Hydrochloric Acid → HCID 52918699, compound

HRID 1476139Notes

Reaction equation

HRID 1476139 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][C:5]1([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([NH:16][C:17](=[O:32])[CH:18]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)[C@@H:19]([CH3:24])[C:20]([F:23])([F:22])[F:21])[CH:10]=2)[CH2:8][CH2:7][CH2:6]1.[OH-].[Na+].Cl>O1CCOCC1>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([C:5]2([CH2:4][C:3]([OH:33])=[O:2])[CH2:6][CH2:7][CH2:8]2)=[CH:10][C:11]=1[NH:16][C:17](=[O:32])[CH:18]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)[C@@H:19]([CH3:24])[C:20]([F:23])([F:22])[F:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58288160HCID 58288160, compound

Product 1

HCID 52918699HCID 52918699, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

38 mg (0.08 mmol) of methyl-[1-(4-chloro-3-{[(3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoyl]amino}phenyl)cyclobutyl]acetate were dissolved in 9.5 ml of dioxane, and 0.15 ml of 1 N aqueous sodium hydroxide solution was added. The mixture was stirred at 80° C. overnight. The reaction mixture was then acidified with 1 N hydrochloric acid to pH 1 and extracted repeatedly with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution, dried over sodium sulphate and concentrated under reduced pressure. The crude product was purified by preparative HPLC. This gave 22 mg (0.05 mmol, 60% of theory) of the target compound.

Workup

  1. extractionextracted repeatedly with ethyl acetate
  2. washThe combined organic phases were washed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-015f3e31eb534fe6b5fcfa39c3a46d91
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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