Potassium Carbonate → N-[1(S)-Ethoxycarbonyl-3-phenylpropyl]-L-alanine
Reaction equation
[CH2:1]([NH:3][C@H:4]([C:13]([OH:15])=[O:14])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].[C:16]1(C)C(S(O[C@H](C)C(OCC2C=CC=CC=2)=O)(=O)=O)=CC=C[CH:21]=1.[C:39](=[O:42])([O-])[O-:40].[K+].[K+]>C(#N)C>[CH2:16]([O:14][C:13]([C@@H:4]([NH:3][C@H:1]([C:39]([OH:40])=[O:42])[CH3:2])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:15])[CH3:21]Participants
5
Procedure
Ethyl (S)-homophenylalanine (I') and benzyl (R)-α-toluenesulfonyloxypropionate (II') in the presence or absence of potassium carbonate were added to acetonitrile (15 ml, bp 82° C.), and refluxed for a predetermined time, while stirring. After completing the reaction, the mixture was concentrated under reduced pressure and water (10 ml) was added to the oily residue. Then the mixture was extracted with toluene (10 ml). The organic layer was concentrated under reduced pressure to remove toluene. The oily residue was subjected to silica gel column chromatography to give the compound N-[(lS)-1-ethoxycarbonyl-3-phenylpropyl]-L-alanine. The reaction conditions are shown in Table 3.
Workup
- temperaturerefluxed for a predetermined time
- customthe reaction
- concentrationthe mixture was concentrated under reduced pressure and water (10 ml)
- additionwas added to the oily residue
- extractionThen the mixture was extracted with toluene (10 ml)
- concentrationThe organic layer was concentrated under reduced pressure
- customto remove toluene
Sources & evidence
- ORD record
- ord-a514b0037b054f80bd8b3b0a39c51b65
- Source dataset
- uspto-grants-1991_10
- Patent number
- US05055588
Reaction notes
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