Dichloromethane → HCID 58288272, compound

HRID 1476131Notes

Reaction equation

HRID 1476131 reaction equation
[Cl-].[NH4+].Cl[C:4]1(Cl)[C:7](=[O:8])[CH2:6][CH:5]1[C:9]1[CH:14]=[CH:13][C:12]([CH:15]([C@@H:21]([CH3:26])[C:22]([F:25])([F:24])[F:23])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:11][CH:10]=1.ClCCl>C1COCC1.[Zn]>[F:23][C:22]([F:24])([F:25])[C@H:21]([CH3:26])[CH:15]([C:12]1[CH:11]=[CH:10][C:9]([CH:5]2[CH2:6][C:7](=[O:8])[CH2:4]2)=[CH:14][CH:13]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 58288163HCID 58288163, compound

Product 1

HCID 58288272HCID 58288272, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

100 ml of saturated aqueous ammonium chloride solution were added to 4.57 g (11.51 mmol) of ethyl (3R)-2-[4-(2,2-dichloro-3-oxocyclobutyl)phenyl]-4,4,4-trifluoro-3-methylbutanoate and 3.76 g (57.5 mmol) of zinc dust in 100 ml of THF, and the mixture was then stirred at 75° C. for 5 h. After cooling to room temperature and addition of dichloromethane, the reaction mixture was washed with water. After separation of the phases, the aqueous phase was back-extracted three times with dichloromethane. The combined organic phases were then dried over magnesium sulphate, filtered and concentrated under reduced pressure. This gave 1.21 g of the title compound (32% of theory).

Workup

  1. temperatureAfter cooling to room temperature
  2. washthe reaction mixture was washed with water
  3. customAfter separation of the phases
  4. extractionthe aqueous phase was back-extracted three times with dichloromethane
  5. dry with materialThe combined organic phases were then dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3aa5870dacb642cfa5ef676ad1e0bcac
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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