Sulfuric Acid → (S)-7-[(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)]-1,2,6,7,8,12b-hexahydro-6-oxopyrido[2,1-a][2]benzazepine

HRID 342898

반응식

HRID 342898 반응식
S(=O)(=O)(O)O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[O:19]=[C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](=[O:29])[N:21]1[C@@H:30]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:31]([N:33]1[CH:38]=[CH:37][CH2:36][CH:35]=[CH:34]1)=[O:32].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.CCCCCC>[O:29]=[C:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:20](=[O:19])[N:21]1[C@H:30]1[CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[CH:34]2[CH2:35][CH2:36][CH:37]=[CH:38][N:33]2[C:31]1=[O:32]

참가 물질

6

반응물 4

HCID 1118Sulfuric AcidHCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 15380836(S)-N-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-1,4-dihydro-pyridine

생성물 1

HCID 9863597(S)-7-[(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)]-1,2,6,7,8,12b-hexahydro-6-oxopyrido[2,1-a][2]benzazepine

시약·촉매·용매 1

HCID 21226206Ethyl acetate hexane용매2회

실험 절차

Combine sulfuric acid (3.0 mL, 96%) and trifluoroacetic anhydride (300 mL). Add (S)-N-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-1,4-dihydro-pyridine (1.0 mmol). After 30 minutes, pour the reaction mixture into mixture of saturated aqueous sodium bicarbonate and ice. Extract with ethyl acetate and then with methylene chloride. Combine the organic layers and filter through a plug of silica gel. Rinse the silica gel with dichloromethane. Evaporate the filtrate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with 10% ethyl acetate/hexane and then 25% ethyl acetate/hexane to give the title compound.

후처리

  1. additionpour the reaction mixture
  2. extractionExtract with ethyl acetate
  3. filtrationfilter through a plug of silica gel
  4. washRinse the silica gel with dichloromethane
  5. customEvaporate the filtrate in vacuo
  6. customto give a residue

출처 및 근거

ORD 기록
ord-3c1672865aea43538351043f1ac29aa6
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05859252

연결된 노트

불러오는 중…