Methanesulfonamide → Tert-butyl [(2-isobutyl-4-(4-methylphenyl)-6-{2-[(methylsulfonyl)amino]-2-oxoethoxy}quinolin-3-yl)methyl]carbamate

HRID 1986436노트

반응식

HRID 1986436 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[C:11]([CH2:32][CH:33]([CH3:35])[CH3:34])=[N:12][C:13]2[C:18]([C:19]=1[C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)=[CH:17][C:16]([O:27][CH2:28][C:29](O)=[O:30])=[CH:15][CH:14]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N(OC(ON2C(=O)CCC2=O)=O)C(=O)C1.[CH3:54][S:55]([NH2:58])(=[O:57])=[O:56].C1CCN2C(=NCCC2)CC1>CN(C)C=O.O>[CH2:32]([C:11]1[C:10]([CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[C:19]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:27][CH2:28][C:29]([NH:58][S:55]([CH3:54])(=[O:57])=[O:56])=[O:30])[CH:17]=2)[N:12]=1)[CH:33]([CH3:35])[CH3:34]

참가 물질

7

반응물 4

HCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 676246Di(succinimido) carbonateHCID 68829615{[3-{[(Tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]oxy}acetic acid

생성물 1

HCID 69152932Tert-butyl [(2-isobutyl-4-(4-methylphenyl)-6-{2-[(methylsulfonyl)amino]-2-oxoethoxy}quinolin-3-yl)methyl]carbamate수율 100.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of {[3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]oxy}acetic acid (0.25 g, 0.52 mmol) in N,N-dimethylformamide (5 ml) was added di(N-succinimidyl) carbonate (0.42 g, 2.6 mmol), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture were added methanesulfonamide (0.25 g, 2.6 mmol) and 1,8-diazabicyclo[5.4.0]-7-undecene (0.40 ml, 2.6 mmol), and the mixture was stirred at 100° C. for 5 hrs. The reaction mixture was cooled to room temperature and water was poured thereinto. The mixture was extracted with ethyl acetate and the extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was crystallized from n-hexane-diisopropyl ether to give tert-butyl [(2-isobutyl-4-(4-methylphenyl)-6-{2-[(methylsulfonyl)amino]-2-oxoethoxy}quinolin-3-yl)methyl]carbamate (0.29 g, yield 98%) as pale-yellow crystals.

후처리

  1. stirringthe mixture was stirred at 100° C. for 5 hrs
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was crystallized from n-hexane-diisopropyl ether

출처 및 근거

ORD 기록
ord-0d1893f1eff04ee09fbc4f021986b1d5
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07547710B2

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