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Sodium Methoxide → HCID 178453509, Verbindung

HRID 717740
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 717740
C[O:2][C:3](=O)[C:4]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:16][CH2:17][CH2:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:10][CH:9]=1)=[CH:5]OC.[Br:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]2[NH:46][C:45]([NH2:47])=[N:44][CH:43]=2)=[CH:38][CH:37]=1.C[O-].[Na+]>C(O)C>[C:30]([O:29][C:27](=[O:28])[N:15]([CH2:14][C:11]1[CH:12]=[CH:13][C:8]([C:4]2[C:3](=[O:2])[N:47]=[C:45]3[NH:46][C:42]([C:39]4[CH:38]=[CH:37][C:36]([Br:35])=[CH:41][CH:40]=4)=[CH:43][N:44]3[CH:5]=2)=[CH:9][CH:10]=1)[CH2:16][CH2:17][CH2:18][NH:19][C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])([CH3:32])([CH3:31])[CH3:33]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 10942334Sodium Methoxide2×HCID 130122555-(4-bromophenyl)-1H-imidazol-2-amineHCID 665788052-(4-{[tert-Butoxycarbonyl-(3-tert-butoxycarbonylamino-propyl)-amino]-methyl}-phenyl)-3-methoxy-acrylic acid methyl ester

Produkt 1

HCID 178453509HCID 178453509, VerbindungAusbeute 52,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702
Ethanol
Lösungsmittel

Versuchsvorschrift

To a mixture of 2-(4-{[tert-Butoxycarbonyl-(3-tert-butoxycarbonylamino-propyl)-amino]-methyl}-phenyl)-3-methoxy-acrylic acid methyl ester (5.70 g, 11.92 mmol), 5-(4-bromo-phenyl)-1H-imidazol-2-ylamine (2.84 g, 11.92 mmol) and ethanol (60 mL) was added a solution of sodium methoxide (12 mL, 0.5 M in methanol, 6 mmol). The resulted mixture was refluxed for 18 h, additional 12 mL of sodium methoxide (0.5 M in methanol, 6 mmol) was added and continued to reflex for 20 h. The reaction was concentrated and diluted with EtOAc (300 mL) and washed with water (200 mL), brine (200 mL). The EtOAc solution was concentrated. The crude product was purified by flash chromatography (0%-8% Methanol in dichloromethane) to give desired product (4.05 g, 52%) as brown solid. 1NMR (300 MHz, CDCl3): δ 7.96 (s, 1H), 7.68 (d, J=8.1 Hz, 2H), 7.54 (m, 2H), 7.35(s, 1H), 7.27 (d, J=8.1 Hz, 2H), 5.25 (br.s, 0.5H), 4.70 (br.s, 0.5H), 4.44 (s, 2H), 3.29 (m, 2H), 3.11 (m, 2H), 1.67 (m, 2H), 1.52 (br.d, 9H), 1.44 (s, 9H). LCMS (EI) m/z: 654 (M+H+).

Aufarbeitung

  1. temperatureThe resulted mixture was refluxed for 18 h
  2. concentrationThe reaction was concentrated
  3. additiondiluted with EtOAc (300 mL)
  4. washwashed with water (200 mL), brine (200 mL)
  5. concentrationThe EtOAc solution was concentrated
  6. customThe crude product was purified by flash chromatography (0%-8% Methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-c658ce91915146a5b9844e4e7bcf37e8
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09193731B2

Notizen zur Reaktion

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