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Ethanol → HCID 136334120, Verbindung

HRID 1297524
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1297524
[CH2:1]([O:8][CH2:9][C:10]([NH:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][C:21]=1[C:22]#[N:23])[CH:18]([NH:24][C:25]1[CH:37]=[CH:36][C:28]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:27][CH:26]=1)[CH2:17][CH2:16]2)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[OH:40].OO.[OH-].[Na+]>O>[CH2:1]([O:8][CH2:9][C:10]1[NH:23][C:22](=[O:40])[C:21]2[C:13](=[CH:14][C:15]3[CH2:16][CH2:17][CH:18]([NH:24][C:25]4[CH:37]=[CH:36][C:28]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:27][CH:26]=4)[C:19]=3[CH:20]=2)[N:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 702EthanolHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 16046384HCID 16046384, Verbindung

Produkt 1

HCID 136334120HCID 136334120, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred, ice-bath cooled mixture of tert-butyl 4-[N-(5-(2-benzyloxy-ethanoylamino)-6-cyanoindan-1-yl)amino]benzoate (3.77 g, 7.59 mmol), EtOH (70 ml), and H2O (11 ml) was added 30% H2O2 (8.05 ml) followed by granulated NaOH pellets (0.640 g, 16.0 mmol). The reaction mixture was stirred at 0° C. for 10 min, then placed in an oil-bath preheated to 55° C. and stirred at this temperature for 1 hour. The solvents were then removed in vacuo; the residue was treated with H2O (80 ml) and the pH was adjusted to ˜5 with 1N HCl. The pale yellow solid was collected by filtration, washed with H2O and dried in vacuo over P2O5 (3.56 g, 95%); mp 194-195° C.; 1H-NMR (250 MHz, DMSO-d6, TMS) 1.52 (s, 9H, C(CH3)3), 1.90 (m), 2.62 (m) (1H each, 7-CH), 2.90-3.17 (m, 2H, 8-CH2), 4.43, 4.60 (2×s, 2H each, PhCH2 and OCH2CO), 5.18 (q, J=7.43 Hz, 1H, 6-CH), 6.79 (d, J=8.8 Hz, 2H, 3′,5′-ArH), 6.87 (d, J=8.0 Hz, 1H, N10—H), 7.34 (m, 5H, PhCH2), 7.54, 7.92 (2×s, 1H each, 5-H and 9-H), 7.68 (d, J=8.9 Hz, 2H, 2′,6′-ArH), 12.20 (s, 1H, CONH); MS (ESI, m/z) 520 {(M+Na)+, 90%,}, 498 {(M+H)+, 100%}; Found: C, 72.13; H, 6.25; N, 8.38; C30H31N3O4 requires C, 72.41; H, 6.28; N, 8.44%.

Aufarbeitung

  1. temperatureTo a stirred, ice-bath cooled
  2. customplaced in an oil-bath
  3. custompreheated to 55° C.
  4. stirringstirred at this temperature for 1 hour
  5. customThe solvents were then removed in vacuo
  6. additionthe residue was treated with H2O (80 ml)
  7. filtrationThe pale yellow solid was collected by filtration
  8. washwashed with H2O
  9. dry with materialdried in vacuo over P2O5 (3.56 g, 95%)

Quellen und Nachweise

ORD-Eintrag
ord-c42088bd315a4a29852b8b0e727d3d10
Quelldatensatz
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07250511B2

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