Triethylamine → 4-[N-[1-[N-(furan-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(2-methanesulonylphenyl)piperidin-3-one

HRID 1392413노트

반응식

HRID 1392413 반응식
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][C:9]1([C:15]([NH:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[S:30]([CH3:33])(=[O:32])=[O:31])[CH2:20][CH:19]2[OH:34])=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7].C(N(CC)CC)C>CS(C)=O.C(OCC)(=O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][C:9]1([C:15]([NH:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[S:30]([CH3:33])(=[O:32])=[O:31])[CH2:20][C:19]2=[O:34])=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7]

참가 물질

5

반응물 2

HCID 8471TriethylamineHCID 693150824-[N-[1-[N-(furan-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(2-methanesulfonylphenyl)piperidin-3-ol

생성물 1

HCID 100056894-[N-[1-[N-(furan-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(2-methanesulonylphenyl)piperidin-3-one수율 41.3%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

To the solution of 4-[N-[1-[N-(furan-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(2-methanesulfonylphenyl)piperidin-3-ol (0.39 g, 0.77 mmol) obtained in Step 5 in 3 ml of dimethylsulfoxide (DMSO), was added 0.4 ml of triethylamine. The reaction mixture was cooled to 0° C. Pyridine-SO3 complex (0.4 g, 2.51 mmol) was added to the reaction mixture, which was then stirred for 2 hours. The reaction mixture was diluted with 20 ml of ethyl acetate, washed with brine. The resulting organic layer was dried and concentrated on sodium sulfate. The resulting residue was purified with column chromatography to give 155 mg of the titled compound as white solid.

후처리

  1. additionPyridine-SO3 complex (0.4 g, 2.51 mmol) was added to the reaction mixture, which
  2. washwashed with brine
  3. customThe resulting organic layer was dried
  4. concentrationconcentrated on sodium sulfate
  5. customThe resulting residue was purified with column chromatography

출처 및 근거

ORD 기록
ord-f105e159cac44c52a52dce0afdcc786a
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07342027B2

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