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.[Cl:17][C:18]1[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[C:19]=1[CH2:20]Br>C(O)C>[CH2:2]([O:4][C:5](=[O:9])[C@@H:6]([CH3:8])[NH:7][CH2:20][C:19]1[C:22]([N+:26]([O-:28])=[O:27])=[CH:23][CH:24]=[CH:25][C:18]=1[Cl:17])[CH3:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 18.24 g of D-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 resulting mixture was heated to 80° C. The solution obtained was added dropwise at this temperature to a solution of 15 g of 2-chloro-6-nitrobenzyl bromide 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 over sodium sulphate and evaporated. The resulting product was purified by chromatography on silica gel with methylene chloride/5% methanol. There were obtained 16 g (93% of theory) of N-(2-chloro-6-nitrobenzyl)-D-alanine ethyl ester; nD25 =1.5247; [α]D =-6.9° (c=1% in ethanol).
Workup
- customThe solution obtained
- 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
- dry with materialdried over sodium sulphate
- customevaporated
- customThe resulting product was purified by chromatography on silica gel with methylene chloride/5% methanol
Sources & evidence
- ORD record
- ord-8f3631eba64e4d3b959b52004ebbed82
- Source dataset
- uspto-grants-1981_03
- Patent number
- US04256748
Linked notes
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