Methyl 2-oxo-3-phenylpropanoate → 3-(S)-amino-1-[1-carboxy-2-phenylethyl]perhydroazepin-2-one
Reaction equation
O=C(CC1C=CC=CC=1)C(OC)=O.C([BH3-])#N.[Na+].C(OC([NH:25][C@H:26]1[CH2:32][CH2:31][CH2:30][CH2:29][N:28]([CH:33]([C:41]([O:43]C)=[O:42])[CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:27]1=[O:45])=O)(C)(C)C>>[NH2:25][C@H:26]1[CH2:32][CH2:31][CH2:30][CH2:29][N:28]([CH:33]([C:41]([OH:43])=[O:42])[CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:27]1=[O:45]Participants
4
Procedure
Methyl 2-oxo-3-phenylpropionate and α-t-Boc-L-lysine are condensed in the presence of sodium cyanoborohydride as described in Example 19. Subsequent ring closure to 3-(S)-t-butoxycarbonylamino-1-[1-carbomethoxy-2-phenylethyl]perhydroazepin-2-one is carried out as described in Example 3. Saponification of the methyl ester followed by removal of the t-butoxycarbonyl group affords 3-(S)-amino-1-[1-carboxy-2-phenylethyl]perhydroazepin-2-one. The caprolactam and 2-oxo-4-phenylbutyric acid are condensed in the presence of sodium cyanoborohydride to yield 1-[1-carboxy-2-phenylethyl]-3-(S)-[(1-carboxy-3-phenylpropyl)amino]perhydroazepin-2-one.
Workup
- customSaponification of the methyl ester followed by removal of the t-butoxycarbonyl group
Sources & evidence
- ORD record
- ord-32c222a3501e4aa18646898ebc0ab78f
- Source dataset
- uspto-grants-1986_12
- Patent number
- US04629787
Reaction notes
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