تفاعل #486525

معادلة التفاعل

2-(R)-[(4-methoxybenzenesulfonyl)(4-picolyl)amino]-2-[(N-(2-(1-naphthyl)-ethoxycarbonyl))-4-piperidinyl] acetic acid

O-t-butylhydroxylamine

N-methylmorpholine

1-hydroxy-7-azabenzotriazole

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

→

N-(t-butyloxy)-2-(R)-[(4-methoxybenzenesulfonyl) (4-picolyl)amino]-2-[(N-(2-(1-naphthyl)-ethoxycarbonyl))-4-piperidinyl]acetamide

المردود 72.3%

المذيبات

ethyl acetate

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   غسيلwashed with water
2. 2
   استخلاصThe aqueous layer is extracted with ethyl acetate
3. 3
   غسيلthe combined organic layers are washed with brine
4. 4
   تجفيفdried over sodium sulfate
5. 5
   تركيزconcentrated in vacuo
6. 6
   أخرىThe crude product is purified by silica gel chromatography (2% methanol in methylene chloride)

الإجراء التجريبي

To a solution of the crude 2-(R)-[(4-methoxybenzenesulfonyl)(4-picolyl)amino]-2-[(N-(2-(1-naphthyl)-ethoxycarbonyl))-4-piperidinyl] acetic acid (6.02 mmol) in methylene chloride (150 ml) is added O-t-butylhydroxylamine (2.27 g, 18.06 mmol), N-methylmorpholine (3.65 g, 36.12 mmol), 1-hydroxy-7-azabenzotriazole (819 mg, 6.02 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.5 g, 7.83 mmol). The reaction mixture is stirred at room temperature for 1.5 hours, diluted with ethyl acetate and washed with water. The aqueous layer is extracted with ethyl acetate, the combined organic layers are washed with brine, dried over sodium sulfate, and concentrated in vacuo. The crude product is purified by silica gel chromatography (2% methanol in methylene chloride) to provide N-(t-butyloxy)-2-(R)-[(4-methoxybenzenesulfonyl) (4-picolyl)amino]-2-[(N-(2-(1-naphthyl)-ethoxycarbonyl))-4-piperidinyl]acetamide (3 g).

المصدر