تفاعل #73667

معادلة التفاعل

2-(tert-butoxycarbonyl(methyl)amino)-4-methylthiazole-5-carboxylic acid

N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate

benzylamine

triethylamine

sodium bicarbonate

→

tert-butyl 5-(benzylcarbamoyl)-4-methylthiazol-2-yl(methyl)carbamate

المردود 31.9%

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   استخلاصThe mixture was extracted with ethyl acetate
2. 2
   تجفيفThe combined organic layer was dried over anhydrous sodium sulfate
3. 3
   ترشيحfiltered
4. 4
   تركيزconcentrated in vacuo
5. 5
   أخرىThe crude product was purified by flash column chromatography
6. 6
   غسيلeluting with ethyl acetate/hexanes (5/95 to 100/0)

الإجراء التجريبي

To a solution of 2-(tert-butoxycarbonyl(methyl)amino)-4-methylthiazole-5-carboxylic acid (0.070 g, 0.26 mmol) in dichloromethane (2 mL) at 0° C. was added N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.15 g, 0.39 mmol), followed by the addition of benzylamine (29.5 μL, 0.27 mmol), 4-dimethylaminopyridine (catalytical amount), and triethylamine (72 μL, 0.52 mmol). The reaction mixture was allowed to warm to ambient temperature over 3 h, followed by the addition of saturated sodium bicarbonate solution. The mixture was extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography eluting with ethyl acetate/hexanes (5/95 to 100/0) to afford tert-butyl 5-(benzylcarbamoyl)-4-methylthiazol-2-yl(methyl)carbamate (0.030 g, 0.083 mmol).

المصدر