HCID 67490967, compound → HCID 67491021, compound

HRID 1917422Notes

Reaction equation

HRID 1917422 reaction equation
C(OC([N:11]1[CH2:17][C@@H:16]2[C@@:13]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])([CH2:14][CH:15]2[CH2:18][F:19])[CH2:12]1)=O)C1C=CC=CC=1.[H][H]>O1CCCC1.[OH-].[Pd+2].[OH-].[C]>[C:24]([O:23][C:21]([NH:20][C@@:13]12[CH2:14][CH:15]([CH2:18][F:19])[C@@H:16]1[CH2:17][NH:11][CH2:12]2)=[O:22])([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 2

HCID 67490967HCID 67490967, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67491021HCID 67491021, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(1S,5R)-3-Benzyloxycarbonyl-1-(tert-butoxycarbonylamino)-6-fluoromethyl-3-azabicyclo[3.2.0]heptane (derived from isomer B) (305 mg, 806 μmol) was dissolved in tetrahydrofuran (6 mL). 20% palladium hydroxide-carbon (50% wet) (100 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 1 M sodium hydroxide solution was added to the residue under ice-cooling, followed by extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 196 mg of the title compound as a colorless syrup.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionA 1 M sodium hydroxide solution was added to the residue under ice-
  4. temperaturecooling
  5. extractionfollowed by extraction with chloroform
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6556432c51034a9e8f552d6640e6f723
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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