Benzyl Benazepril → 3-[[1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetic acid

HRID 2418722Notes

Reaction equation

HRID 2418722 reaction equation
C([O:8][C:9]([CH2:11][N:12]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH2:16][CH2:15][CH:14]([NH:23][CH:24]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:13]1=[O:38])=[O:10])C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[C:9]([CH2:11][N:12]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH2:16][CH2:15][CH:14]([NH:23][CH:24]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:13]1=[O:38])([OH:10])=[O:8]

Participants

5

Reactant 2

HCID 20244751Benzyl BenazeprilHCID 178418361HCID 178418361, compound

Product 1

HCID 23113-[[1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-benzyloxycarbonylmethyl-3-(1-ethoxycarbonyl-3-phenylpropylamino)-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one (isomer B of example 3, 0.9 g) in ethanol (150 ml) was hydrogenated at room temperature and atmospheric pressure, using 10% palladium on charcoal (0.5 g) as catalyst. After uptake of hydrogen had ceased, the catalyst was filtered off, and the solvent removed under reduced pressure to give a solid. This material was triturated with ether (8 ml) to give the title compound melting at 138°-140° and identical to the compound obtained in Example 1.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationthe catalyst was filtered off
  3. customthe solvent removed under reduced pressure
  4. customto give a solid
  5. customThis material was triturated with ether (8 ml)

Sources & evidence

ORD record
ord-019a917b163247c4bebea8c31b3b92fc
Source dataset
uspto-grants-1984_09
Patent number
US04473575

Reaction notes

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