Acetic Anhydride → N-(Trifluoroacetyl)-L-Asp-L-Phe-OMe
Reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]([NH:5][C@H:6]([C:11]([OH:13])=O)[CH2:7][C:8]([OH:10])=[O:9])=[O:4].C(OC(=O)C)(=O)C.C([O-])(=O)C.[Na+].Cl.[CH3:29][O:30][C:31](=[O:41])[C@H:32]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[NH2:33]>C(O)(=O)C>[CH3:29][O:30][C:31](=[O:41])[C@H:32]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[NH:33][C:11](=[O:13])[C@H:6]([CH2:7][C:8](=[O:9])[OH:10])[NH:5][C:3](=[O:4])[C:2]([F:1])([F:15])[F:14]Participants
Procedure
In 63.3 g of acetic acid, 22.9 g (0.1 mole) of N-trifluoroacetyl-L-aspartic acid was suspended and 10.2 g (0.1 mole) of acetic anhydride was added. The mixture was warmed to 55°-60° C. and stirred for 6 hours at the same temperature. After finishing the reaction, the resulting mixture was cooled to 15°-20° C. and then 9.2 g (0.11 mole) of sodium acetate and 20.5 g (0.095 mole) of L-phenylalanine methyl ester hydrochloride were successively added at the same temperature. The reaction was carried out for 2 hours with stirring at the same temperature. Precipitated crystals were filtered, washed and dried. Crystals of N-trifluoroacetyl-α-L-aspartyl-L-phenylalanine methyl ester were obtained in the yield of 29.3 g (79.0% yield on L-phenylalanine methyl ester hydrochloride). The crystals thus obtained were analyzed by high performance liquid chromatography to find α-isomer alone.
Workup
- temperatureThe mixture was warmed to 55°-60° C.
- customthe reaction
- temperaturethe resulting mixture was cooled to 15°-20° C.
- waitThe reaction was carried out for 2 hours
- stirringwith stirring at the same temperature
- customPrecipitated crystals
- filtrationwere filtered
- washwashed
- customdried
Sources & evidence
- ORD record
- ord-a179c5463b0244a5b3ced63ca5b9cefd
- Source dataset
- uspto-grants-1994_04
- Patent number
- US05302743
Reaction notes
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