3-azido-1-benzyloxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one → (3-Amino-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)acetic acid
Reaction equation
[N:1]([CH:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=2[N:6]([CH2:15][C:16]([O:18]CC2C=CC=CC=2)=[O:17])[C:5]1=[O:26])=[N+]=[N-]>C(O)C.[Pd]>[NH2:1][CH:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=2[N:6]([CH2:15][C:16]([OH:18])=[O:17])[C:5]1=[O:26]Participants
Procedure
A solution of 3-azido-1-benzyloxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one (14.0 g, 0.04 mol) in ethanol (300 ml) was hydrogenated for 25 hours on a Parr shaker at 45 psi at room temperature using 5% Pd-C (2.0 g) as catalyst. The catalyst was filtered off and the solvent removed under reduced pressure. The residue was dissolved in water (500 ml) and the solution extracted with dichloromethane (2×400 ml). The aqueous solution was filtered, and evaporated under reduced pressure. Ethanol (50 ml) was added and the solution evaporated under reduced pressure. More ethanol (50 ml) was added, and the evaporation repeated. The residue was recrystallized from ethanol/ethyl acetate to give 3-amino-1-carboxymethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one, m.p. 147°-50°.
Workup
- filtrationThe catalyst was filtered off
- customthe solvent removed under reduced pressure
- dissolutionThe residue was dissolved in water (500 ml)
- extractionthe solution extracted with dichloromethane (2×400 ml)
- filtrationThe aqueous solution was filtered
- customevaporated under reduced pressure
- additionEthanol (50 ml) was added
- customthe solution evaporated under reduced pressure
- additionMore ethanol (50 ml) was added
- customthe evaporation
- customThe residue was recrystallized from ethanol/ethyl acetate
Sources & evidence
- ORD record
- ord-922a54f276aa49498e966a43999c34ac
- Source dataset
- uspto-grants-1986_03
- Patent number
- US04575503
Reaction notes
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