HCID 67490940, compound → HCID 67491146, compound

HRID 1917352Notes

Reaction equation

HRID 1917352 reaction equation
C(OC([N:11]1[CH2:18][C@@H:17]2[C@@:13]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])([CH2:14][CH2:15][C@@H:16]2[F:19])[CH2:12]1)=O)C1C=CC=CC=1.[H][H]>CO.[C].[Pd]>[C:24]([O:23][C:21]([NH:20][C@@:13]12[CH2:14][CH2:15][C@H:16]([F:19])[C@@H:17]1[CH2:18][NH:11][CH2:12]2)=[O:22])([CH3:27])([CH3:25])[CH3:26]

Participants

5

Reactant 2

HCID 67490940HCID 67490940, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67491146HCID 67491146, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

{(1S,5R,6S)-1-tert-Butoxycarbonylamino-6-fluoro-3-azabicyclo[3,3,0]octan-3-yl}carboxylic acid benzyl ester (132 mg, 0.35 mmol) was dissolved in methanol (10 mL). 10% palladium-carbon (M, wet) (50 mg) was added, and the mixture was stirred in a hydrogen atmosphere for three hours. 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 85 mg of the title compound as a colorless oil.

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-ee1cb3a0f0814ea394bdd9075fb02fe8
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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