Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](I)[CH:5]=[CH:6][C:7]=1[Cl:8].[NH2:10][C@H:11]([C:13]([OH:15])=[O:14])[CH3:12].C1(NN=CC2C=CC=CC=2O)C=CC=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl>O.[Cu]I.CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][CH:11]([CH3:12])[C:13]([OH:15])=[O:14])[CH:5]=[CH:6][C:7]=1[Cl:8]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 3,4-dichloroiodobenzene (1.50 g, 5.50 mmol), L-alanine (734 mg, 8.25 mmol), copper(I) iodide, 2-hydroxybenzaldehyde phenylhydrazone (233 mg, 1.10 mmol), tri-potassium phosphate (3.50 g, 16.5 mmol), and N,N-dimethylformamide (8 mL) was stirred at 80° C. for 40 h, then after cooling diluted with water and acidified to pH 3 by addition of 37% aq. HCl solution. The mixture was extracted with EtOAc, the organic phase was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; EtOAc) afforded the title compound (1.08 g, 67%) as a 71:29 mixture of the (S) and (R) stereoisomers (accordingly, when D-alanine was used instead of L-alanine as starting material, the title compound was obtained as a 29:71 mixture of the (S) and (R) stereoisomers). Brown solid, MS: 232.1 (M−H)−.
Workup
- temperatureafter cooling
- extractionThe mixture was extracted with EtOAc
- washthe organic phase was washed with brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-ba18df7b02184cea8a743c632e8b5caf
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08138175B2
Linked notes
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