Acetic Acid → HCID 58288311, compound

HRID 1476140Notes

Reaction equation

HRID 1476140 reaction equation
C(O)(=O)C.Cl.[Cl:6][C:7]1[CH:21]=[CH:20][C:10]([CH2:11][C@@H:12]([CH2:18][CH3:19])[C:13]([O:15]CC)=[O:14])=[CH:9][C:8]=1[NH:22][C:23](=[O:38])[C@H:24]([C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1)[C@@H:25]([CH3:30])[C:26]([F:29])([F:28])[F:27]>O>[Cl:6][C:7]1[CH:21]=[CH:20][C:10]([CH2:11][C@@H:12]([CH2:18][CH3:19])[C:13]([OH:15])=[O:14])=[CH:9][C:8]=1[NH:22][C:23](=[O:38])[C@H:24]([C:31]1[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=1)[C@@H:25]([CH3:30])[C:26]([F:29])([F:28])[F:27]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 58288196HCID 58288196, compound

Product 1

HCID 58288311HCID 58288311, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

15.2 ml of acetic acid and 7.6 ml of concentrated hydrochloric acid were added to 1.96 g (3.89 mmol) of ethyl (+)-(2R)-2-(4-chloro-3-{[(2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoyl]amino}benzyl)butanoate. The reaction mixture was stirred under reflux for 5 h (bath temperature 140° C.). After cooling, water was added. The mixture was extracted repeatedly with dichloromethane, and the combined organic phases were washed with saturated sodium chloride solution, dried over sodium sulphate and concentrated under reduced pressure. Chromatography of the residue on silica gel (mobile phase cyclohexane/ethyl acetate 10:1→2:1) gave 1.46 g (78.6% of theory) of the title compound.

Workup

  1. temperatureAfter cooling
  2. extractionThe mixture was extracted repeatedly with dichloromethane
  3. washthe combined organic phases were washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4333e6a963254424aa46c94df07b1b69
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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