تفاعل #7768

معادلة التفاعل

2-(tert-Butoxycarbonyl)amino-5-trifluoromethylbenzoic acid

→

title compound

المردود 14.0%

2-Isopropoxycarbonylamino-5-trifluoromethyl-benzoic acid

المردود 14.0%

المذيبات

HCl

dioxane

ظروف التفاعل

المعالجة

1. 1
   تركيزthe solution was concentrated to a white solid
2. 2
   workup.DISSOLUTIONA portion of this material (900 mg) was dissolved in THF (10 mL)
3. 3
   workup.ADDITIONwater (2 mL), and Et3N (1.8 mL) prior to the addition of 1M i-propyl chloroformate (4.5 mL) in toluene
4. 4
   workup.ADDITIONwas added
5. 5
   غسيلThe EtOAc layer was washed with 1N HCl and brine before it
6. 6
   أخرىwas dried
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated to a crude material
9. 9
   أخرىThis material was crystallized with CH2Cl2

الإجراء التجريبي

2-(tert-Butoxycarbonyl)amino-5-trifluoromethylbenzoic acid (6.0 g) was dissolved in 4M HCl (4 mL) in dioxane. After 3 h, the solution was concentrated to a white solid. A portion of this material (900 mg) was dissolved in THF (10 mL), water (2 mL), and Et3N (1.8 mL) prior to the addition of 1M i-propyl chloroformate (4.5 mL) in toluene. The reaction was stirred for 4 h before EtOAc was added. The EtOAc layer was washed with 1N HCl and brine before it was dried, filtered, and concentrated to a crude material. This material was crystallized with CH2Cl2 to give the title compound (800 mg). MS found: (2M−1)−=581.2.

المصدر