반응 #68205

반응 방정식

(1-(2-(4-((tert-butoxycarbonyl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-2-oxo-1,2-dihydroquinolin-5-yloxy)acetic acid

methylamine hydrochloride

(benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate

N,N-diisopropylethylamine

→

tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(5-((methylamino)carbonylmethyloxy)-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

수율 99.0%

용매

water

N,N-dimethylformamide

반응 조건

후처리

1. 1
   workup.ADDITIONwere added
2. 2
   추출extracted with a mixture of ethyl acetate
3. 3
   세척The organic layer was washed sequentially with water and aqueous saturated sodium chloride solution
4. 4
   건조dried over anhydrous magnesium sulfate
5. 5
   기타the solvent was removed under reduced pressure
6. 6
   기타The residue thus obtained
7. 7
   기타was purified by silica gel column chromatography [Silica Gel; Kanto Chemical Co., Inc., Silica Gel 60, eluent; chloroform: methanol=10:1]

실험 절차

To 5 mL of an N,N-dimethylformamide solution containing 88 mg of (1-(2-(4-((tert-butoxycarbonyl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-2-oxo-1,2-dihydroquinolin-5-yloxy)acetic acid and 41 mg of methylamine hydrochloride, 183 mg of (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate and 0.11 mL of N,N-diisopropylethylamine were added, and stirred at room temperature overnight. The reaction mixture was poured into water, and extracted with a mixture of ethyl acetate: toluene=5:1. The organic layer was washed sequentially with water and aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [Silica Gel; Kanto Chemical Co., Inc., Silica Gel 60, eluent; chloroform: methanol=10:1], to give 89 mg of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(5-((methylamino)carbonylmethyloxy)-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a pale yellow foam.

출처