Diethyl Ether → HCID 13243535, compound

HRID 482750Notes

Reaction equation

HRID 482750 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][CH2:10][CH:9]([NH:18][CH:19]([C:28]([O:30]CC2C=CC=CC=2)=[O:29])[CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:8]1=[O:38])=[O:5])[CH3:2].CCOCC>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([CH2:6][N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][CH2:10][CH:9]([NH:18][CH:19]([C:28]([OH:30])=[O:29])[CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:8]1=[O:38])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 20244767HCID 20244767, compound

Product 1

HCID 13243535HCID 13243535, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-Ethoxycarbonylmethyl-3-(1-benzyloxycarbonyl-3-phenylpropylamino-2,3,4,5-tetrahydro-1H-[1]-benzazepine-2-one (isomer B of Example 20, 1.1 g) in ethanol (150 ml) was hydrogenated at room temperature and atmospheric pressure using palladium on charcoal (0.5 g) was catalyst. After uptake of hydrogen had terminated, the catalyst was filtered off, and the solvent removed under reduced pressure to give a semi-solid. Trituration with ether (30 ml) yielded isomer B of the title compound, m.p. 175°-177° C.

Workup

  1. customwas hydrogenated at room temperature
  2. customAfter uptake of hydrogen had terminated
  3. filtrationthe catalyst was filtered off
  4. customthe solvent removed under reduced pressure
  5. customto give a semi-solid

Sources & evidence

ORD record
ord-9c1f7c8fc4c048cd995aa00d7a576947
Source dataset
uspto-grants-1986_03
Patent number
US04575503

Reaction notes

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