Water → HCID 52918570, compound

HRID 1476144Notes

Reaction equation

HRID 1476144 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:14][CH2:15][CH3:16])[CH2:9][C:10]([O:12]C)=[O:11])=[CH:4][C:3]=1[NH:17][C:18](=[O:33])[C@H:19]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)[C@@H:20]([CH3:25])[C:21]([F:24])([F:23])[F:22].S(=O)(=O)(O)O.O>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:14][CH2:15][CH3:16])[CH2:9][C:10]([OH:12])=[O:11])=[CH:4][C:3]=1[NH:17][C:18](=[O:33])[C@H:19]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)[C@@H:20]([CH3:25])[C:21]([F:24])([F:23])[F:22]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 58288419HCID 58288419, compound

Product 1

HCID 52918570HCID 52918570, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
140 °C

Procedure

1.50 g (2.97 mmol) of methyl 3-(4-chloro-3-{[(2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoyl]amino}phenyl)hexanoate (diastereomer mixture) were dissolved in 5 ml of acetic acid, 5 ml of 30% strength sulphuric acid were added and the mixture was heated at reflux (bath temperature about 140° C.). After 1.5 h, a further 2.5 ml of acetic acid were added, and the reaction mixture was stirred under reflux for another 2.5 h. After cooling, the mixture was allowed to stand at RT overnight, then added to water and extracted three times with ethyl acetate. The combined organic phases were washed with 5% strength sodium bicarbonate solution and sat. sodium chloride solution, dried over magnesium sulphate and concentrated under reduced pressure, and the residue was dried under high vacuum. This gave 1.44 g of the target product (98.8% of theory).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for another 2.5 h
  3. temperatureAfter cooling
  4. waitto stand at RT overnight
  5. extractionextracted three times with ethyl acetate
  6. washThe combined organic phases were washed with 5% strength sodium bicarbonate solution and sat. sodium chloride solution
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated under reduced pressure
  9. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-2fd86d236f554bffba1ffd5e7833d605
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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