반응 #49221

반응 방정식

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

수율 97.0%

3-(dipropylcarbamoyl)benzoic acid

수율 97.0%

용매

H2O

acetonitrile

반응 조건

후처리

1. 1
   온도the mixture was warmed up
2. 2
   기타acetonitrile was removed
3. 3
   workup.ADDITIONEthyl acetate (600 mL) was added
4. 4
   세척the mixture was washed with 3N HCl, H2O
5. 5
   건조dried over Na2SO4
6. 6
   농축concentrated in vacuo

실험 절차

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.

출처