Sodium Bicarbonate → 2-[8-[N-benzyl-N-[(2S)-2-hydroxy-3-(1H-indol-5-yloxy)propyl]amino]-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy]-N-butylacetamide

HRID 2299670노트

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HRID 2299670 반응식
[CH2:1]([NH:8][CH:9]1[CH2:15][C:14]2[CH:16]=[C:17]([O:20][CH2:21][C:22]([NH:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:23])[CH:18]=[CH:19][C:13]=2[CH2:12][CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:29]1[C:37]2[C:32](=[CH:33][C:34]([O:38][CH2:39][C@H:40]3[O:42][CH2:41]3)=[CH:35][CH:36]=2)[CH:31]=[CH:30]1.FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([N:8]([CH:9]1[CH2:15][C:14]2[CH:16]=[C:17]([O:20][CH2:21][C:22]([NH:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:23])[CH:18]=[CH:19][C:13]=2[CH2:12][CH2:11][CH2:10]1)[CH2:41][C@H:40]([OH:42])[CH2:39][O:38][C:34]1[CH:33]=[C:32]2[C:37](=[CH:36][CH:35]=1)[NH:29][CH:30]=[CH:31]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 516892Sodium BicarbonateHCID 2733225Ytterbium triflateHCID 180072362-(8-benzylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy)-N-butylacetamideHCID 23553465(2S)-1-(1H-indol-5-yloxy)-2,3-epoxypropane

생성물 1

HCID 693300382-[8-[N-benzyl-N-[(2S)-2-hydroxy-3-(1H-indol-5-yloxy)propyl]amino]-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy]-N-butylacetamide수율 53.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Under nitrogen, to a solution of 2-(8-benzylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy)-N-butylacetamide (200 mg) and (2S)-1-(1H-indol-5-yloxy)-2,3-epoxypropane (130 mg) in dichloromethane (10 ml) was added ytterbium(III) trifluoromethanesulfonate (33 mg) at room temperature, and the mixture was stirred at the same temperature for 3 hours. The resulting mixture was poured into saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed (hexane-ethyl acetate) over silica gel to afford 2-[8-[N-benzyl-N-[(2S)-2-hydroxy-3-(1H-indol-5-yloxy)propyl]amino]-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy]-N-butylacetamide (160 mg)

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed (hexane-ethyl acetate) over silica gel

출처 및 근거

ORD 기록
ord-133d4c4268f6466d9902700eff7f2dfa
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06495546B1

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