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Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → (9S)-1-Acetylamino-9-ethyl-2,3-dihydro-9-hydroxy-1H, 12H-benzo[de]pyrano[3',4':6,7]indolizino[1,2-b]quinoline-10,13-(9H,15H)-dione

HRID 1683472
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HRID 1683472 반응식
[CH2:1]([C@:3]1([OH:19])[C:15]2[CH:14]=[C:13]3[N:9]([CH2:10][CH2:11][C:12]3=O)[C:8](=[O:17])[C:7]=2[CH2:6][O:5][C:4]1=[O:18])[CH3:2].[C:20]([NH:23][CH:24]1[CH2:33][CH2:32][C:31]2[C:26](=[C:27]([NH2:34])[CH:28]=[CH:29][CH:30]=2)[C:25]1=O)(=[O:22])[CH3:21].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C=CC=CC=1>[C:20]([NH:23][CH:24]1[C:25]2=[C:11]3[CH2:10][N:9]4[C:13](=[CH:14][C:15]5[C@:3]([CH2:1][CH3:2])([OH:19])[C:4](=[O:18])[O:5][CH2:6][C:7]=5[C:8]4=[O:17])[C:12]3=[N:34][C:27]3[CH:28]=[CH:29][CH:30]=[C:31]([C:26]=32)[CH2:32][CH2:33]1)(=[O:22])[CH3:21]
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참가 물질

5

반응물 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)2회HCID 10220900(4S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano(3,4-f)indolizine-3,6,10(4H)-trioneHCID 120472992-Acetylamino-8-amino-1-tetralone

생성물 1

HCID 12047300(9S)-1-Acetylamino-9-ethyl-2,3-dihydro-9-hydroxy-1H, 12H-benzo[de]pyrano[3',4':6,7]indolizino[1,2-b]quinoline-10,13-(9H,15H)-dione

시약·촉매·용매 1

HCID 1140
Toluene
용매

실험 절차

361 mg of (S)-4-ethyl-4-hydroxy-7,8-dihydro-1H-pyrano-[3,4-f]indolizine-3,6,10(4H)-trione (hereinafter abbreviated as "trione") was added to the solution of 300 mg of the compound prepared in (4) above in 200 ml of toluene. The mixture was heated under reflux using a Deanstark apparatus for 10 minutes. To the mixture was added 1 mg of pyridinium-p-toluenesulfonate (hereinafter abbreviated as "PPTS") and the mixture was refluxed while stirring for a further 24 hours. After cooling, the residue obtained by removing toluene by concentration was suspended into 300 ml of chloroform-methanol (10:1) solvent. Insoluble substances were removed and the residue was powdered with methanol to obtain 336 mg of the title compound.

후처리

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. customfor 10 minutes
  4. temperaturewas refluxed
  5. temperatureAfter cooling
  6. customthe residue obtained
  7. customby removing toluene
  8. concentrationby concentration
  9. customInsoluble substances were removed

출처 및 근거

ORD 기록
ord-ecc3c06835564971a9185cc765b8b6e9
출처 데이터셋
uspto-grants-1997_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05637770

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