반응 #49219

반응 방정식

methylbutylamine

( 1 )

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

Methyl 3-(butyl(methyl)carbamoyl)benzoate

3-(methoxycarbonyl)benzoic acid

Hunig's base

HATU

→

title compound

3-(butyl(methyl)carbamoyl)benzoic acid

용매

dichloromethane

DMF

반응 조건

후처리

1. 1
   workup.ADDITIONwas then added
2. 2
   workup.STIRRINGthe reaction mixture was stirred at rt for 3 h
3. 3
   기타Dichloromethane was removed
4. 4
   workup.ADDITIONethyl acetate (300 mL) was added
5. 5
   세척the mixture was washed with 1N HCl, sodium carbonate solution, H2O
6. 6
   기타dried
7. 7
   농축concentrated

실험 절차

Step F (1): Methyl 3-(butyl(methyl)carbamoyl)benzoate. To a solution of 3-(methoxycarbonyl)benzoic acid (1.8 g, 10 mmol) in dichloromethane (40 mL) and DMF (20 mL) was added Hunig's base (2.58 g, 20 mmol) to make a clear solution and HATU (4.18 g, 11 mmol) was then added. After stirring for 10 min, the reaction mixture was added methylbutylamine (1.13 g, 13 mmol) and the reaction mixture was stirred at rt for 3 h. Dichloromethane was removed and ethyl acetate (300 mL) was added and the mixture was washed with 1N HCl, sodium carbonate solution, H2O, dried and concentrated to give the title compound ready for next step without purification: 1H NMR (CDCl3, 500 MHz) δ 0.79-0.98 (3H, m), 1.15 (1H, m), 1.41 (1H, brd s), 1.52 (1H, brd s), 1.64 (1H, m), 2.92-3.07 (2H, m), 3.21 (1H, brd s), 3.53 (1H, brd s), 3.91 (3H, s), 7.47 (1H, m), 7.58 (1H, d, J=10 Hz), 8.05-8.07 (2H, m).

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