Dichloromethane → HCID 86661756, compound

HRID 1845943Notes

Reaction equation

HRID 1845943 reaction equation
C([O:8][CH2:9][CH:10]=[CH:11][C@H:12]([NH:14][C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])[CH3:13])C1C=CC=CC=1.[H][H].ClCCl>C(OCC)(=O)C.[C].[Pd]>[F:17][C:16]([F:18])([F:19])[C:15]([NH:14][C@H:12]([CH3:13])[CH2:11][CH2:10][CH2:9][OH:8])=[O:20]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 86661753HCID 86661753, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86661756HCID 86661756, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

The product (1.0 g) obtained in Step 1 was dissolved in ethyl acetate (10 mL). To the solution, 10% palladium-carbon (300 mg) was added, and the mixture was stirred at 70° C. for 3 hours in a hydrogen atmosphere. After the completion of reaction, the mixture was returned to room temperature, and dichloromethane (5 mL) was added, followed by filtration through celite. The filtrate was concentrated under reduced pressure, and the obtained residue was dissolved in methanol. 10% palladium-carbon (200 mg) was added again thereto, and the mixture was stirred at 70° C. for 16 hours in a hydrogen atmosphere. The mixture was returned to room temperature, and dichloromethane (5 mL) was added, followed by filtration through celite. The filtrate was concentrated under reduced pressure to obtain the compound of interest as a colorless oil (676 mg, 98.3%).

Workup

  1. customAfter the completion of reaction
  2. customwas returned to room temperature
  3. filtrationfollowed by filtration through celite
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. dissolutionthe obtained residue was dissolved in methanol
  6. addition10% palladium-carbon (200 mg) was added again
  7. customwas returned to room temperature
  8. additiondichloromethane (5 mL) was added
  9. filtrationfollowed by filtration through celite
  10. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-060e9d162baa4a2e9c5897649e997abc
Source dataset
uspto-grants-2015_02
Patent number
US08951997B2

Reaction notes

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