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 1481938ノート

反応式

HRID 1481938 の反応式
[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

参加物

6

反応物 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

生成物 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]carbamate収率 65%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c88dbb2d473c41b5bd7c0da3ad8487b0
出典データセット
uspto-grants-2016_08
特許番号
US09409888B2

反応ノート

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