Reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:9])[C@H:6]([CH3:8])[NH2:7])[CH3:3].C(N(CC)CC)C.Br[CH2:18][C:19]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:28]>C(O)C>[CH2:2]([O:4][C:5](=[O:9])[C@H:6]([CH3:8])[NH:7][CH2:18][C:19]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:28])[CH3:3]Participants
Conditions
- Temperature
- 80 °C
Procedure
18.24 g of L-alanine ethyl ester hydrochloride in 60 ml of ethanol was added dropwise to a mixture of 25 ml of triethylamine in 60 ml of ethanol and the mixture was heated to 80° C. The resulting solution was added dropwise at this temperature to a solution of 15 g of α-bromo-2-chloro-6-nitrotoluene in 60 ml of ethanol. The mixture was stirred at 80° C. overnight and then evaporated to dryness. The residue was treated with 150 ml of deionised water and extracted twice with 100 ml of methylene chloride. The methylene chloride extracts were washed with water, dried and evaporated. The resulting product was purified by chromatography on silica gel with methylene chloride/5% methanol. There were obtained 15.75 g (91% of theory) of N-(2-chloro-6-nitrobenzyl)-L-alanine ethyl ester; nD20 =1.5267.
Workup
- customevaporated to dryness
- additionThe residue was treated with 150 ml of deionised water
- extractionextracted twice with 100 ml of methylene chloride
- washThe methylene chloride extracts were washed with water
- customdried
- customevaporated
- customThe resulting product was purified by chromatography on silica gel with methylene chloride/5% methanol
Sources & evidence
- ORD record
- ord-b36b9db07ec04c54a12306153c9f1ab9
- Source dataset
- uspto-grants-1981_03
- Patent number
- US04256748
Linked notes
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