반응 #8944

반응 방정식

potassium carbonate

N-[3(S)-[N,N-bis(phenylmethyl)amino]-2(R)-hydroxy-4-phenylbutyl]-N-isobutylamine

1,3-benzodioxole-5-sulfonyl chloride

oxalic acid

→

sulfonamide

수율 105.0%

1-[N-[(1,3-benzodioxol-5-yl)sulfonyl]-N-(2-methylpropyl)amino]-3(S)-[bis(phenylmethyl)amino]-4-phenyl-2(R)-butanol

수율 105.0%

용매

water

Ethyl acetate

water

1,4-dioxane

1,4-dioxane

반응 조건

후처리

1. 1
   기타To a 5000 mL, 3-necked flask fitted with a mechanical stirrer
2. 2
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 18 hours
3. 3
   workup.STIRRINGstirring
4. 4
   workup.WAITcontinued for another 1 hour
5. 5
   기타The aqueous layer was separated
6. 6
   추출further extracted with ethyl acetate (200 mL)
7. 7
   세척The combined ethyl acetate layers were washed with 25% brine solution (500 mL)
8. 8
   건조dried over anhydrous magnesium sulfate
9. 9
   여과After filtering
10. 10
    세척washing the magnesium sulfate with ethyl acetate (200 mL)
11. 11
    기타the solvent in the filtrate was removed under reduced pressure

실험 절차

To a 5000 mL, 3-necked flask fitted with a mechanical stirrer was added N-[3(S)-[N,N-bis(phenylmethyl)amino]-2(R)-hydroxy-4-phenylbutyl]-N-isobutylamine.oxalic acid salt (354.7 g, 0.7 mole) and 1,4-dioxane (2000 mL). A solution of potassium carbonate (241.9 g, 1.75 moles) in water (250 mL) was then added. The resultant heterogeneous mixture was stirred for 2 hours at room temperature followed by the addition of 1,3-benzodioxole-5-sulfonyl chloride (162.2 g, 0.735 mole) dissolved in 1,4-dioxane (250 mL) over 15 minutes. The reaction mixture was stirred at room temperature for 18 hours. Ethyl acetate (1000 mL) and water (500 mL) were charged to the reactor and stirring continued for another 1 hour. The aqueous layer was separated and further extracted with ethyl acetate (200 mL). The combined ethyl acetate layers were washed with 25% brine solution (500 mL) and dried over anhydrous magnesium sulfate. After filtering and washing the magnesium sulfate with ethyl acetate (200 mL), the solvent in the filtrate was removed under reduced pressure yielding the desired sulfonamide as an viscous yellow foamy oil (440.2 g 105% yield). HPLC/MS (electrospray) (m/z 601 [M+H]+].

출처