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Trifluoroacetic acid → N1-(4-Cyanobutyl)-N1-(phenylmethoxy)-N4-[5-[(phenylmethoxy)amino]pentyl]butanediamide

HRID 2380432
ノート
印刷プレビュー

反応式

HRID 2380432 の反応式
C(O)(C(F)(F)F)=O.C(OC([N:15]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:42])[CH2:23][CH2:24][C:25](=[O:41])[N:26]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:27][CH2:28][CH2:29][CH2:30][C:31]#[N:32])=O)(C)(C)C>C(Cl)Cl>[CH2:34]([O:33][N:26]([C:25](=[O:41])[CH2:24][CH2:23][C:22](=[O:42])[NH:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][NH:15][O:43][CH2:44][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)[CH2:27][CH2:28][CH2:29][CH2:30][C:31]#[N:32])[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 1098482417-(tert-Butoxycarbonyl)-6,17-bis(benzyloxy)-7,10-dioxo-6,11,17-triazaheptadecanenitrile

生成物 1

HCID 10929123N1-(4-Cyanobutyl)-N1-(phenylmethoxy)-N4-[5-[(phenylmethoxy)amino]pentyl]butanediamide収率 87%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

6,17-Bis(benzyloxy)-7,10-dioxo-6,11,17-triazaheptadecane-nitrile (9) was synthesized by slowly adding trifluoroacetio acid (TFA, 40 mL) to (8) (6.00 g, 10.1 mmol) in CH2Cl2 (100 mL). The solution was stirred at 0° C. for 15 minutes and at room temperature for 30 minutes. Solvents were removed by rotary evaporation, aqueous NaHCO3 was added and the product was extracted into CHCl3. Column chromatography on silica gel, eluting with 5% CH3OH/CHCl3, afforded 4.3 g (87%) of (9): NMR δ 1.2-1.8 (m, 10 H), 2.2-3.3 (mr 10 H), 3.62 (t, 2 H, J=7), 4.63 (s, 2 H), 4.82 (s, 2 H), 5.5 (br s, 1 H), 5.87 (br s, 1 H), 7.15-7.35 (m, 10 H). Anal. calcd. for C28H38N4O4 : C, 67.99; H, 7.74; N, 11.33. Found: C, 67.82; H, 7.79; N, 11.29 [Bergeron et al, Tetrahedron (1989), supra].

後処理

  1. custom6,17-Bis(benzyloxy)-7,10-dioxo-6,11,17-triazaheptadecane-nitrile (9) was synthesized
  2. customSolvents were removed by rotary evaporation, aqueous NaHCO3
  3. additionwas added
  4. extractionthe product was extracted into CHCl3
  5. washColumn chromatography on silica gel, eluting with 5% CH3OH/CHCl3

出典と根拠

ORDレコード
ord-4f773eb5d4844bda8b36c689e4a35858
出典データセット
uspto-grants-1994_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05367113

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート