Citric Acid → L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-
Reaction equation
[C:1]([O:5][C:6](ON=C(C(C)=O)C(OCC)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:19][C@H:20]([C:28]([OH:30])=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)(C)(C)C.O>[C:1]([O:5][C:6]([NH:19][C@H:20]([C:28]([OH:30])=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
Procedure
A solution of ethyl 2-tert-butoxycarbonyloxyiminoacetoacetate (646 mg.) in a mixture of tert-butyl alcohol (5 ml.) and water (5 ml.) was added at once to a solution of L-phenylalanine (330 mg.) and triethylamine (0.28 ml.) in a mixture of tert-butyl alcohol (8 ml.) and water (8 ml.) at room temperature. The mixture was stirred for 2 hours at room temperature. Water (100 ml.) was added to the reaction mixture and the mixture was adjusted to pH 7 with a 0.5M citric acid aqueous solution and washed twice with ethyl acetate (40 ml). The aqueous layer was adjusted to pH 3 with a 0.5M citric acid aqueous solution, followed by addition of a sodium chloride aqueous solution, and extracted twice with ethyl acetate (40 ml.). The extract was washed with water and dried. The solvent was distilled off under reduced pressure to give N-tert-butoxycarbonyl-L-phenylalanine (286 mg.).
Workup
- washwashed twice with ethyl acetate (40 ml)
- additionfollowed by addition of a sodium chloride aqueous solution
- extractionextracted twice with ethyl acetate (40 ml.)
- washThe extract was washed with water
- customdried
- distillationThe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-ab50ec2d5a514fd19686d59c9ea4f54c
- Source dataset
- uspto-grants-1978_04
- Patent number
- US04083848
Reaction notes
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