4-[(1-Carboxy-1-methylethyl)amino]-2-fluorobenzoic acid synthesis
- Product Name:4-[(1-Carboxy-1-methylethyl)amino]-2-fluorobenzoic acid
- CAS Number:1332524-02-3
- Molecular formula:C11H12FNO4
- Molecular Weight:241.22
62-57-7
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Yield:1332524-02-3 81.7%
Reaction Conditions:
with copper(l) iodide;dimethylaminoacetic acid;copper;potassium carbonate in N,N-dimethyl-formamide at 110; for 16 h;Inert atmosphere;Large scale;
Steps:
1 Example 1
Preparation of 4-(1-carboxyl-1-methyl-ethylamino)-2-fluoro-benzoic Acid
To the reaction kettle, was introduced nitrogen gas, to which were added N,N-dimethylformamide (20 L), water (2 L), 4-bromo-2-fluorobenzoic acid (2.0 kg), 2-methylalanine (2.82 kg), N,N-dimethylglycine (474 g), potassium carbonate (6.31 kg), copper powder (116 g), and CuI (348 g).
Under the protection of nitrogen, the mixture was stirred at 110° C. for 16 hours.
The reaction solution was cooled to the room temperature, and then ice water (30 L) was added.
The pH value of solution was adjusted to 4-5 by drop adding 6N ice hydrochloric acid, and extracted with ethyl acetate twice (20 L*2).
The organic phase was combined, and washed with water (5 L) once.
The organic phase was concentrated to dry, to which was added dichloromethane (15 L) for pulping, then filtered, dried in vacuum at 40° C., to provide the target compound 1.797 kg, with a yield of 81.7%.
References:
US2020/87261,2020,A1 Location in patent:Paragraph 0030; 0031