反応 #49221

反応方程式

3-amino-5-(methoxycarbonyl)benzoic acid

(2R,4R)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

( 2 )

(2R,4R)-4-(allyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

3-bromo-5-(methoxycarbonyl)benzoic acid

n-butyl nitrite

→

title compound

収率 97.0%

3-(dipropylcarbamoyl)benzoic acid

収率 97.0%

溶媒

H2O

acetonitrile

反応条件

後処理

1. 1
   温度the mixture was warmed up
2. 2
   その他acetonitrile was removed
3. 3
   workup.ADDITIONEthyl acetate (600 mL) was added
4. 4
   洗浄the mixture was washed with 3N HCl, H2O
5. 5
   乾燥dried over Na2SO4
6. 6
   濃縮concentrated in vacuo

実験手順

Step G (2): 3-bromo-5-(methoxycarbonyl)benzoic acid. To a mixture of copper (II) bromide (5.5 g, 24.6 mmol), n-butyl nitrite (3.17 g, 30.75 mmol) and acetonitrile (300 mL) was added 3-amino-5-(methoxycarbonyl)benzoic acid (Step G (1), 4.0 g, 20.5 mmol) in aceonitrile (300 mL) over 30 min at 0° C. and the mixture was warmed up and stirred at rt for 3 h. H2O was added and acetonitrile was removed. Ethyl acetate (600 mL) was added and the mixture was washed with 3N HCl, H2O, dried over Na2SO4, and concentrated in vacuo to give the title compound (97% yield): 1H NMR (CDCl3, 500 MHz) δ ppm 3.96 (3H, s), 8.41 (1H, s), 8.41 (1H, s), 8.67 (1H, m). MS (ESI) (M−H)− 259.02.

出典