Ethyl Acetate → HCID 23114189, compound

HRID 1787322Notes

Reaction equation

HRID 1787322 reaction equation
[CH3:1][C:2]([CH3:33])([CH3:32])[CH2:3][C:4]([NH:6][C:7]1[C:8]([CH3:31])=[C:9]([CH3:30])[C:10]2[O:14][CH2:13][CH:12]([C:15]3[CH:16]=[C:17](/[CH:21]=[CH:22]/[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:18]=[CH:19][CH:20]=3)[C:11]=2[C:28]=1[CH3:29])=[O:5].C(OCC)(=O)C>[Pd].C(O)C>[CH3:32][C:2]([CH3:1])([CH3:33])[CH2:3][C:4]([NH:6][C:7]1[C:8]([CH3:31])=[C:9]([CH3:30])[C:10]2[O:14][CH2:13][CH:12]([C:15]3[CH:16]=[C:17]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:18]=[CH:19][CH:20]=3)[C:11]=2[C:28]=1[CH3:29])=[O:5]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 69200058HCID 69200058, compound

Product 1

HCID 23114189HCID 23114189, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixed solution of ethyl (2E)-3-(3-(5-((3,3-dimethylbutanoyl)amino)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-3-yl)phenyl)acrylate (400 mg, 0.89 mmol) obtained in Example 177 and 10% palladium on carbon (water content: 50%, 40 mg) in ethanol (3 mL)-ethyl acetate (5 mL) was stirred at room temperature for 2 hours under a hydrogen atmosphere. The reaction solution was filtered through celite and the filtrate was concentrated under reduced pressure to obtain 326 mg (yield: 81%) of the title compound. Melting point: 136-138° C. (ethyl acetate-hexane).

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bd339f4723704fef8073fbaad9f7ff6a
Source dataset
uspto-grants-2009_03
Patent number
US07507841B2

Reaction notes

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