HCID 66685757, compound → HCID 66685765, compound

HRID 1778380Notes

Reaction equation

HRID 1778380 reaction equation
C(OC([NH:11][C:12]1[C:21]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[C:20]2[C:15]([C:16]3[CH:32]=[CH:31][O:30][C:17]=3[C:18](=[O:29])[O:19]2)=[CH:14][CH:13]=1)=O)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[NH2:11][C:12]1[C:21]([C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23])=[C:20]2[C:15]([C:16]3[CH:32]=[CH:31][O:30][C:17]=3[C:18](=[O:29])[O:19]2)=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 66685757HCID 66685757, compound2×

Product 1

HCID 66685765HCID 66685765, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of tert-butyl 7-benzyloxycarbonylamino-4-oxo-4H-furo[2,3-c]chromene-6-carboxylate (Intermediate 58, 0.318 g) in ethyl acetate (10 mL) was added a slurry of 10% palladium on activated carbon (0.032 g) in ethyl acetate (10 mL). The flask was de-gassed and filled with hydrogen and the mixture stirred at room temperature for 90 minutes. The mixture was filtered through Celite and washed with ethyl acetate. The filtrate was concentrated in vacuo to give tert-butyl 7-amino-4-oxo-4H-furo[2,3-c]chromene-6-carboxylate (0.214 g) as a white solid.

Workup

  1. customThe flask was de-gassed
  2. additionfilled with hydrogen
  3. filtrationThe mixture was filtered through Celite
  4. washwashed with ethyl acetate
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-551464cf333a4a34bfea3adf91ca3367
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

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