تفاعل #91020

معادلة التفاعل

tert-butyl 4-(3,5-dichloro-4-ethoxybenzamido)-2-methoxybenzoate

tert-Butyl 4-(3,5-dichloro-4-ethoxybenzamido)-2-methoxybenzoate

boron trichloride

water

NaHCO3

→

4-(3,5-dichloro-4-ethoxybenzamido)-2-hydroxybenzoic acid

المردود 24.0%

المذيبات

DCM

DCM

ظروف التفاعل

المعالجة

1. 1
   workup.WAITat RT for 2 h
2. 2
   درجة الحرارةThe reaction mixture was cooled to 0° C.
3. 3
   ترشيحThe resulting white precipitate was collected by filtration
4. 4
   غسيلwashed with water (2 mL)
5. 5
   أخرىThe solid was dried
6. 6
   أخرىpurified by capture and release on SAX
7. 7
   غسيلeluting with 5% AcOH in THF

الإجراء التجريبي

A solution of tert-butyl 4-(3,5-dichloro-4-ethoxybenzamido)-2-methoxybenzoate (5) (55 mg, 0.13 mmol) in DCM (5 mL) was cooled to 0° C. and treated dropwise with a solution of 1 M boron trichloride in DCM (349 μL, 349 μmol). The reaction mixture was stirred at 0° C. for 1 h and then at RT for 2 h. The reaction mixture was cooled to 0° C. and water (0.5 mL) and sat. aq. NaHCO3 (2 mL) were added. The resulting white precipitate was collected by filtration and washed with water (2 mL). The solid was dried, then purified by capture and release on SAX, eluting with 5% AcOH in THF to afford 4-(3,5-dichloro-4-ethoxybenzamido)-2-hydroxybenzoic acid (AAA-057) (11 mg, 24%) as a white solid: m/z 370 [M+H]+ (ES+), 368 [M−H]− (ES−); 1H-NMR (400 MHz, DMSO-d6) δ: 10.51 (1H, s), 8.06 (2H, s), 7.76 (1H, d), 7.48 (1H, d), 7.28 (1H, dd), 4.14 (2H, q), 1.91 (1H, s), 1.40 (3H, t), 1.35 (1H, s).

المصدر