Formic Acid → (S)-7-[(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)]-1,2,3,4,6,7,8,12b-octahydro-6-oxopyrido[2,1-a][2]benzazepine-4-carboxylic acid

HRID 342899

반응식

HRID 342899 반응식
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C@H:12]1[CH2:18][C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[CH:15]2[CH2:23][CH2:24][CH:25]=[CH:26][N:14]2[C:13]1=[O:27].S(=O)(=O)(O)O.[CH:33]([OH:35])=[O:34].O>C(OCC)(=O)C.CCCCCC>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]1[CH2:18][C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[CH:15]2[CH2:23][CH2:24][CH2:25][C@@H:26]([C:33]([OH:35])=[O:34])[N:14]2[C:13]1=[O:27]

참가 물질

6

반응물 4

HCID 284Formic AcidHCID 962WaterHCID 1118Sulfuric AcidHCID 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

생성물 1

HCID 22874156(S)-7-[(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)]-1,2,3,4,6,7,8,12b-octahydro-6-oxopyrido[2,1-a][2]benzazepine-4-carboxylic acid

시약·촉매·용매 1

HCID 21226206Ethyl acetate hexane용매

실험 절차

Combine (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 (32 mg, 0.09 mmol) and sulfuric acid (1.0 mL, 95-98%) in a pressure vessel. Add 96% formic acid (200 μL) and quickly seal the vessel. After 18 hours, add water (10 mL). Extract the reaction mixture with ethyl acetate. Extract the organic layer with saturated aqueous potassium carbonate solution (5×10 mL). Combine the aqueous layers and carefully acidify with aqueous 12M hydrochloric acid solution. Extract with chloroform (5×15 mL). Combine the organic layers, dry over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 2/1 ethyl acetate/hexane containing 0.5% acetic acid to give the title compound. Rf =0.14 (silica gel, 2/1 ethyl acetate/hexane containing 0.5% acetic acid).

후처리

  1. customquickly seal the vessel
  2. extractionExtract the reaction mixture with ethyl acetate
  3. extractionExtract the organic layer with saturated aqueous potassium carbonate solution (5×10 mL)
  4. extractionExtract with chloroform (5×15 mL)
  5. dry with materialCombine the organic layers, dry over MgSO4
  6. filtrationfilter
  7. customevaporate in vacuo
  8. customto give a residue

출처 및 근거

ORD 기록
ord-70d1aa59fa844dd099f5747c743178a5
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05859252

연결된 노트

불러오는 중…