Benzyl Benazepril → 3-[[1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetic acid
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
Procedure
A solution of 1-benzyloxycarbonylmethyl-3-(1-ethoxycarbonyl-3-phenylpropylamino)-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one (isomer A of example 3; 1.2 g) in ethanol (125 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 1-carboxymethyl-3-(1-ethoxycarbonyl-3-phenylpropylamino)-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one melting at 126°-129°, and being the lower melting racemic isomer A.
Workup
- customwas hydrogenated at room temperature
- filtrationthe catalyst was filtered off
- customthe solvent removed under reduced pressure
- customto give a solid
- customThis material was triturated with ether (8 ml)
Sources & evidence
- ORD record
- ord-6990ae43a77b45748bc196f6675ee3dc
- Source dataset
- uspto-grants-1984_09
- Patent number
- US04473575
Reaction notes
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