HCID 67491019, compound → HCID 67490955, compound

HRID 1917354Notes

Reaction equation

HRID 1917354 reaction equation
C(OC([N:11]1[CH2:18][C@@H:17]2[C@@:13]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])([CH2:14][CH2:15][C:16]2([F:20])[F:19])[CH2:12]1)=O)C1C=CC=CC=1.[H][H]>CO.[C].[Pd]>[C:25]([O:24][C:22]([NH:21][C@@:13]12[CH2:14][CH2:15][C:16]([F:20])([F:19])[C@@H:17]1[CH2:18][NH:11][CH2:12]2)=[O:23])([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 2

HCID 67491019HCID 67491019, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67490955HCID 67490955, compoundYield 102.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

[(1S,5R)-1-tert-Butoxycarbonylamino-6,6-difluoro-3-azabicyclo[3,3,0]octan-3-yl]carboxylic acid benzyl ester (65.0 mg, 0.16 mmol) was dissolved in methanol (10 mL). 10% palladium-carbon (50% wet) (20 mg) was added, and the mixture was stirred in a hydrogen atmosphere for one hour. The catalyst was removed by filtration, and then the filtrate was concentrated under reduced pressure. A 1N sodium hydroxide solution was added, followed by extraction with chloroform. After drying over anhydrous sodium sulfate and filtration, the filtrate was concentrated under reduced pressure to give 43 mg of the title compound as a colorless solid.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionA 1N sodium hydroxide solution was added
  4. extractionfollowed by extraction with chloroform
  5. dry with materialAfter drying over anhydrous sodium sulfate and filtration
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b0bd61e1fccd44ada0c9c1744b4e755a
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

Loading…