N-(N-Formyl-L-alpha-aspartyl)-3-phenyl-L-alanine → L-Aspartyl-L-phenylalanine
Reaction equation
C([NH:3][C@H:4]([C:9]([NH:11][C@H:12]([C:20]([OH:22])=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[CH2:5][C:6](=[O:8])[OH:7])=O>Cl.O>[NH2:3][C@H:4]([C:9]([NH:11][C@H:12]([C:20]([OH:22])=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[CH2:5][C:6](=[O:7])[OH:8]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 15 °C
Procedure
45.5 g of formyl-α-L-aspartyl-L-phenylalanine is dissolved in concentrated hydrogen chloride (18.2 ml) and water (141 ml). The mixture is treated at 60° C. for 4 hours to remove the formyl group. 11.7 g of 50% caustic solution is added into the resulting solution and cooled to 15° C. to obtain a precipitate of α-L-aspartyl-L-phenylalanine. After filtration, the precipitate is washed with 10 ml of water at 5° C. and dried to obtain 25.2 g (0.090 mole) of the desired product. The remaining filtrate is mixed with 50% caustic solution (6.5 g) and cooled to obtain the precipitate by filtration. The precipitate is washed with water (10 ml) at 5° C. and dried to obtain additional α-L-aspartyl-L-phenylalanine (12.2 g, 0.043 mole).
Workup
- additionThe mixture is treated at 60° C. for 4 hours
- customto remove the formyl group
- addition11.7 g of 50% caustic solution is added into the resulting solution
Sources & evidence
- ORD record
- ord-57e1a9ae06694e73bd52e8bc91e8f509
- Source dataset
- uspto-grants-1988_07
- Patent number
- US04760164
Reaction notes
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