Ethyl Acetate → HCID 68512028, compound

HRID 1256875Notes

Reaction equation

HRID 1256875 reaction equation
[CH2:1]([N:3]([CH2:33][CH3:34])[C:4](=[O:32])[CH:5]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=1)[C:6]([NH:8][S:9]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=1)(=[O:11])=[O:10])=[O:7])[CH3:2].C(OCC)(=O)C>C(O)C.[Pd]>[NH2:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][CH:5]([C:6]([NH:8][S:9]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)(=[O:11])=[O:10])=[O:7])[C:4]([N:3]([CH2:1][CH3:2])[CH2:33][CH3:34])=[O:32])=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 68506138HCID 68506138, compound

Product 1

HCID 68512028HCID 68512028, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a mixed suspension of the compound (2.53 g) obtained in Example 6 in ethanol (200 mL)/ethyl acetate (100 mL) was added 10% palladium/carbon (500 mg), and the mixture was heated under reflux under hydrogen atmosphere for 6 hr. After allowing to cool to room temperature, insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure to give the title compound (2.37 g) as a white powder. In some cases, the compound was further converted to a hydrochloride salt with 4 mol/L hydrochloric acid/ethyl acetate and used.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux under hydrogen atmosphere for 6 hr
  3. custominsoluble material was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5e5880bcfc3647548cd97fab955ec759
Source dataset
uspto-grants-2013_06
Patent number
US08461209B2

Reaction notes

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