1,1'-Carbonyldiimidazole → HCID 178432062, 화합물

HRID 1384296노트

반응식

HRID 1384296 반응식
[N+:1]([O-:20])([O:3][CH2:4][CH:5]1[C:11]2=[N:12][C:13]([CH3:19])=[C:14](C(O)=O)[CH:15]=[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:2].C1N=CN([C:26]([N:28]2[CH:32]=[N:31]C=C2)=[O:27])C=1.[NH2:33]C(N)=N.C1COCC1>C1COCC1>[N+:1]([O-:20])([O:3][CH2:4][CH:5]1[C:11]2=[N:12][C:13]([CH3:19])=[C:14]([NH:33][C:32]([N:28]=[C:26]=[O:27])=[NH:31])[CH:15]=[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:2]

참가 물질

5

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 21186707HCID 21186707, 화합물HCID 86757137HCID 86757137, 화합물

생성물 1

HCID 178432062HCID 178432062, 화합물수율 51.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

In an atmosphere of argon, 28% sodium methoxide methanol solution (1.58 ml, 8.19 mmol) was dissolved in anhydrous methanol (8.0 ml) at room temperature, and the solution was mixed with guanidine hydrochloride (782.4 mg, 8.19 mmol) at 0° C. and stirred at the same temperature for 1 hour. The thus precipitated sodium chloride was removed by filtration using a glass filter and the resulting filtrate was evaporated under reduced pressure to obtain free guanidine. In an atmosphere of argon, (3-carboxy-2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl)methyl nitrate (310.0 mg, 1.17 mmol) were suspended in anhydrous THF (8.0 ml), mixed with CDI (291.2 mg, 1.76 mmol) at room temperature and then stirred at 50° C. for 1 hour. The reaction solution was added dropwise to the previously obtained guanidine THF suspension (5.0 ml), and the mixture was stirred at room temperature for 2.5 hours. The solvent was evaporated under reduced pressure, and the resulting residue was mixed with water and extracted with ethyl acetate. The thus obtained organic layer was washed with saturated sodium bicarbonate aqueous solution, water and saturated brine in that order and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, the resulting residue was purified by a silica gel column chromatography (chloroform:methanol=20:1) and then the thus obtained crystals were washed with ether to obtain the title compound (192.1 mg, 51.1%) as white powder.

후처리

  1. stirringthe mixture was stirred at room temperature for 2.5 hours
  2. customThe solvent was evaporated under reduced pressure
  3. additionthe resulting residue was mixed with water
  4. extractionextracted with ethyl acetate
  5. washThe thus obtained organic layer was washed with saturated sodium bicarbonate aqueous solution, water and saturated brine in that order
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe resulting residue was purified by a silica gel column chromatography (chloroform:methanol=20:1)
  9. washthe thus obtained crystals were washed with ether

출처 및 근거

ORD 기록
ord-1c392e07cd004319ba2201a9642ab20f
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06258829B1

반응 노트

불러오는 중…