Sodium Carbonate → N-[(3,5-Dimethylphenoxy)acetyl]-L-glutamic acid
Reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].C(=O)([O-])[O-].[Na+].[Na+].[CH3:17][C:18]1[CH:19]=[C:20]([CH:26]=[C:27]([CH3:29])[CH:28]=1)[O:21][CH2:22][C:23](Cl)=[O:24]>C(#N)C>[CH3:17][C:18]1[CH:19]=[C:20]([CH:26]=[C:27]([CH3:29])[CH:28]=1)[O:21][CH2:22][C:23]([NH:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5]([OH:7])=[O:6])=[O:24]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3,5-dimethylphenoxyacetic acid (9.0 g, 50 mmole) in benzene (100 mL) was added thionyl chloride (10.89 mL). The resulting mixture was refluxed for 2 hr, then the benzene was removed by distillation. The residual material was dried in vacuo to give 3,5-dimethylphenoxyacetyl chloride, which was dissolved in 20 ml of acetonitrile and used in situ. L-Glutamic acid (8.8 g, 60 mmole) was dissolved in a solution of sodium carbonate (12.72 g, 150 mL, 120 mmole) and the 3,5-dimethylphenoxyacetyl chloride in the acetonitrile solution was slowly added while the pH 8 was adjusted from time-to-time by adding sodium carbonate solution. The reaction mixture was stirred at room temperature for 2 hr, and acidified to pH 2 to give a solid precipitate. The solid precipitate was collected by filtration, treated with hot benzene, filtered, again and washed again with benzene to give Intermediate 31 (9.2 g).
Workup
- customto give a solid precipitate
- filtrationThe solid precipitate was collected by filtration
- additiontreated with hot benzene
- filtrationfiltered
- washagain and washed again with benzene
Sources & evidence
- ORD record
- ord-8743d97502104cee886442ce20c71b6f
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06897227B2
Reaction notes
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