تفاعل #69737

معادلة التفاعل

2,4-bis-benzyloxy-5-isopropenyl-benzoic acid

4-hydroxyisoindoline hydrobromide

N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride

1-hydroxybenzotriazole

triethylamine

→

(2,4-bis-benzyloxy-5-isopropenyl-phenyl)-(4-hydroxy-1,3-dihydro-isoindol-2-yl)-methanone

المردود 96.3%

المذيبات

N,N-dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   أخرىThe solvent was removed in vacuo
2. 2
   workup.ADDITIONthe residue was treated with a saturated aqueous solution of sodium hydrogen carbonate (200 ml)
3. 3
   ترشيحThe mixture was filtered
4. 4
   غسيلthe solid material was washed copiously with water
5. 5
   أخرىsucked dry under reduced pressure
6. 6
   أخرىdried in a vacuum oven at 50° C. overnight

الإجراء التجريبي

A mixture of 2,4-bis-benzyloxy-5-isopropenyl-benzoic acid (8.1 g, 21.65 mmol), 4-hydroxyisoindoline hydrobromide (4.91 g, 22.73 mmol), N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (5.0 g, 25.98 mmol), 1-hydroxybenzotriazole (3.5 g, 25.98 mmol) and triethylamine (6 ml, 43.3 mmol) in N,N-dimethylformamide (50 ml) was stirred at room temperature for 16 hours. The solvent was removed in vacuo and the residue was treated with a saturated aqueous solution of sodium hydrogen carbonate (200 ml). The mixture was filtered, the solid material was washed copiously with water, sucked dry under reduced pressure and dried in a vacuum oven at 50° C. overnight to afford (2,4-bis-benzyloxy-5-isopropenyl-phenyl)-(4-hydroxy-1,3-dihydro-isoindol-2-yl)-methanone (10.25 g, 96%) as a pale tan solid. 1H NMR (DMSO-d6) (mixture of amide rotamers) 9.68 and 9.60 (1H, 2×br s), 7.45-7.25 (10H, m), 7.20-7.00 (3H, m), 6.82 and 6.72 (1H, 2×d), 6.68 (1H, m), 5.23 and 5.22 (2H, 2×s), 5.18 (2H, s), 5.11 (1H, s), 5.09 (1H, s), 4.77 and 6.67 (2H, 2×s), 4.53 and 4.44 (2H, 2×s), 2.04 (3H, s). MS: [M+H]+ 492.

المصدر