Cesium carbonate → tert-butyl N-[(3S)-5-[(6-bromo-2-methoxy-1-naphthyl)methyl]-1-[4-[(3S)-5-[(6-bromo-2-methoxy-1-naphthyl)methyl]-3-(tert-butoxycarbonylamino)-4-oxo-2,3-dihydro-1,5-benzodiazepine-1-carbonyl]benzoyl]-4-oxo-2,3-dihydro-1,5-benzodiazepin-3-yl]carbamate

HRID 1481938노트

반응식

HRID 1481938 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:15](=[O:16])[NH:14][C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[N:11]([C:21]([C:23]2[CH:50]=[CH:49][C:26]([C:27]([N:29]3[C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=4[NH:33][C:32](=[O:40])[C@@H:31]([NH:41][C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[CH2:30]3)=[O:28])=[CH:25][CH:24]=2)=[O:22])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:51][C:52]1[CH:53]=[C:54]2[C:59](=[CH:60][CH:61]=1)[C:58]([CH2:62]Cl)=[C:57]([O:64][CH3:65])[CH:56]=[CH:55]2.[C:66](=[O:69])([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[Br:51][C:52]1[CH:53]=[C:54]2[C:59](=[CH:60][CH:61]=1)[C:58]([CH2:62][N:33]1[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[N:29]([C:27](=[O:28])[C:26]3[CH:25]=[CH:24][C:23]([C:21]([N:11]4[C:12]5[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=5[N:14]([CH2:62][C:58]5[C:59]6[C:54](=[CH:53][C:52]([Br:51])=[CH:61][CH:60]=6)[CH:55]=[CH:56][C:57]=5[O:69][CH3:66])[C:15](=[O:16])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:10]4)=[O:22])=[CH:50][CH:49]=3)[CH2:30][C@H:31]([NH:41][C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[C:32]1=[O:40])=[C:57]([O:64][CH3:65])[CH:56]=[CH:55]2

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 7371226-Bromo-1-(chloromethyl)-2-methoxynaphthaleneHCID 90220967tert-butyl N-[(3S)-5-[4-[(3S)-3-(tert-butoxycarbonylamino)-2-oxo-3,4-dihydro-1H-1,5-benzodiazepine-5-carbonyl]benzoyl]-2-oxo-3,4-dihydro-1H-1,5-benzodiazepin-3-yl]carbamate

생성물 1

HCID 90220903tert-butyl N-[(3S)-5-[(6-bromo-2-methoxy-1-naphthyl)methyl]-1-[4-[(3S)-5-[(6-bromo-2-methoxy-1-naphthyl)methyl]-3-(tert-butoxycarbonylamino)-4-oxo-2,3-dihydro-1,5-benzodiazepine-1-carbonyl]benzoyl]-4-oxo-2,3-dihydro-1,5-benzodiazepin-3-yl]carbamate수율 65%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

tert-Butyl N-[(3S)-5-[4-[(3S)-3-(tert-butoxycarbonylamino)-2-oxo-3,4-dihydro-1H-1,5-benzodiazepine-5-carbonyl]benzoyl]-2-oxo-3,4-dihydro-1H-1,5-benzodiazepin-3-yl]carbamate (27.6 mg, 0.0403 mmol), 6-bromo-1-(chloromethyl)-2-methoxynaphthalene (25.3 mg, 0.0887 mmol), and cesium carbonate (39.4 mg, 0.121 mmol) where combined in DMF (2 mL) and stirred at room temperature for 16 h. The mixture was diluted with ethyl acetate, washed with water, brine and dried over anhydrous magnesium sulfate. Concentration gave an oil that was chromatographed over silica gel to give tert-butyl N-[(3S)-5-[(6-bromo-2-methoxy-1-naphthyl)methyl]-1-[4-[(3S)-5-[(6-bromo-2-methoxy-1-naphthyl)methyl]-3-(tert-butoxycarbonylamino)-4-oxo-2,3-dihydro-1,5-benzodiazepine-1-carbonyl]benzoyl]-4-oxo-2,3-dihydro-1,5-benzodiazepin-3-yl]carbamate (31 mg, 65%) as a white foam.

후처리

  1. washwashed with water, brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationConcentration
  4. customgave an oil that
  5. customwas chromatographed over silica gel

출처 및 근거

ORD 기록
ord-c88dbb2d473c41b5bd7c0da3ad8487b0
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409888B2

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