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

HRID 2380432
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HRID 2380432 반응식
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
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참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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].

후처리

  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

출처 및 근거

ORD 기록
ord-4f773eb5d4844bda8b36c689e4a35858
출처 데이터셋
uspto-grants-1994_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05367113

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