Hydrochloric Acid → HCID 67336959, 화합물

HRID 1678326노트

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HRID 1678326 반응식
[Cl-:1].[NH3+:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:10]=[NH+:11][CH:12]=[CH:13][CH:14]=1)=O.[Cl-].[CH:16]([C:18]1[O:22][C:21]([C:23]2[CH:27]=[CH:26][S:25][C:24]=2[C:28]([O:30][CH3:31])=[O:29])=[CH:20][CH:19]=1)=O.Cl>C(O)(C)C>[ClH:1].[ClH:1].[N:11]1[CH:12]=[CH:13][CH:14]=[C:9]([C:7]2[C:6](=[CH:16][C:18]3[O:22][C:21]([C:23]4[CH:27]=[CH:26][S:25][C:24]=4[C:28]([O:30][CH3:31])=[O:29])=[CH:20][CH:19]=3)[CH2:5][CH2:4][CH2:3][N:2]=2)[CH:10]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 2797068Methyl 3-(5-formylfuran-2-yl)thiophene-2-carboxylateHCID 673376573-(5-Ammoniopentanoyl)pyridinium chloride

생성물 1

HCID 67336959HCID 67336959, 화합물수율 97.7%

시약·촉매·용매 1

HCID 3776Isopropanol용매

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온도
80 °C

실험 절차

3-(5-Ammoniopentanoyl)pyridinium chloride (99 mg, 0.39 mmol) and methyl 3-(5-formyl-2-furyl)thiophene-2-carboxylate (102 mg, 0.43 mmol) were combined in a reaction vessel and treated with isopropanol (6 mL). The reaction vessel was sealed and the reaction was heated to 80° C. with stirring overnight. The reaction was cooled to room temperature. The precipitate was recovered by vacuum filtration, then treated with saturated NaHCO3(aq) and extracted three times with EtOAc. The EtOAc extracts were washed with brine, combined, dried over Na2SO4, filtered, concentrated under reduced pressure, and eluted through a 20 gram column of silica gel with 99:1:0.1 CH2Cl2:MeOH:NH4OH (1 liter). The recovered material was dissolved into MeOH and treated with 2 eq. of 6 N HCl(aq). This solution was concentrated under reduced pressure and the recovered material was dissolved into hot isopropanol to re-crystallize. Crystals were recovered by vacuum filtration, washed with a 20 isopropanol in hexane solution, and then with ether, then dried under vacuum giving 86 mg (48%) of an orange solid. LC-MS: RT=5.25 min, [M+H]+=379.0.

후처리

  1. customThe reaction vessel was sealed
  2. temperatureThe reaction was cooled to room temperature
  3. filtrationThe precipitate was recovered by vacuum filtration
  4. additiontreated with saturated NaHCO3(aq)
  5. extractionextracted three times with EtOAc
  6. washThe EtOAc extracts were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. washeluted through a 20 gram column of silica gel with 99:1:0.1 CH2Cl2
  11. dissolutionThe recovered material was dissolved into MeOH
  12. concentrationThis solution was concentrated under reduced pressure
  13. dissolutionthe recovered material was dissolved into hot isopropanol
  14. customto re-crystallize
  15. filtrationCrystals were recovered by vacuum filtration
  16. washwashed with a 20 isopropanol in hexane solution
  17. dry with materialwith ether, then dried under vacuum

출처 및 근거

ORD 기록
ord-1fe955d13c8d4b6a8a7126a3afef2f68
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008499B2

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