Triethylamine → 2-{3-[3-(1H-Benzotriazol-5-yl)-ureido]-2-oxo-7-phenyl-5-o-tolyl-azepan-1-yl}-N-tert-butyl-acetamide

HRID 429724ノート

反応式

HRID 429724 の反応式
[N:1]1[C:5]2=[CH:6][CH:7]=[C:8](C(O)=O)[CH2:9][C:4]2=[N:3][N:2]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:20])C=CC=CC=1.C([N:32]([CH2:35]C)CC)C.[C:37]([NH:41][C:42](=[O:66])[CH2:43][N:44]1[CH:50]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH2:49][CH:48]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=2[CH3:63])[CH2:47][CH:46]([NH2:64])[C:45]1=[O:65])([CH3:40])([CH3:39])[CH3:38]>O1CCCC1.C1C=CC=CC=1>[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:32][C:35](=[O:20])[NH:64][CH:46]3[CH2:47][CH:48]([C:57]4[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=4[CH3:63])[CH2:49][CH:50]([C:51]4[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=4)[N:44]([CH2:43][C:42]([NH:41][C:37]([CH3:40])([CH3:38])[CH3:39])=[O:66])[C:45]3=[O:65])=[CH:9][C:4]=2[N:3]=[N:2]1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 15908914N-(t-Butyl)-2-oxo-3-amino-5-(2-methylphenyl)-7-phenyl-2,3,4,5,6,7-hexahydroazepin-1-yl ethanoic amideHCID 534427314H-Benzo[d][1,2,3]triazole-5-carboxylic acid

生成物 1

HCID 1784241622-{3-[3-(1H-Benzotriazol-5-yl)-ureido]-2-oxo-7-phenyl-5-o-tolyl-azepan-1-yl}-N-tert-butyl-acetamide

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a 35 mL round-bottomed flank equipped with nitrogen inlet and condenser were added 40 mg (0.25 mmol) benzotriazole-5-carboxylic acid, 10 mL dry benzene, 10 mL dry tetrahydrofuran, 0.058 mL (0.27 mmol) diphenylphosphoryl azide, and 0.034 mL (0.27 mmol) triethylamine. The reaction was refluxed for 1.5 hour, cooled briefly, and 100 mg (0.25 mmol) N-(t-butyl)-2-oxo-3-amino-5-(2-methylphenyl)-7-phenyl-2,3,4,5,6,7-hexahydroazepin-1-yl ethanoic amide (the more polar isomer from the preceding example) was added and refluxing continued for 10 hours. The reaction was cooled and evaporated the resulting residue was chromatographed on silica gel with methanol/methylene chloride as eluent to afford the title compound as a white amorphous solid, 53 mg (37%).

後処理

  1. customTo a 35 mL round-bottomed flank equipped with nitrogen inlet and condenser
  2. temperatureThe reaction was refluxed for 1.5 hour
  3. temperaturecooled briefly
  4. temperaturerefluxing
  5. temperatureThe reaction was cooled
  6. customevaporated the resulting residue
  7. customwas chromatographed on silica gel with methanol/methylene chloride as eluent

出典と根拠

ORDレコード
ord-df9717887386411981caebee88efaea1
出典データセット
uspto-grants-2001_11
特許番号
US06319915B1

反応ノート

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