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Ethyl Bromide → [3-(Anthracen-9-ylmethyl-ethyl-amino)-propyl]-(3-tert-butoxycarbonylamino-propyl)-carbamic acid tert-butyl ester

HRID 12994
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 12994
[CH2:1](Br)[CH3:2].[C:4]([O:8][C:9](=[O:41])[N:10]([CH2:22][CH2:23][CH2:24][NH:25][CH2:26][C:27]1[C:28]2[C:33]([CH:34]=[C:35]3[C:40]=1[CH:39]=[CH:38][CH:37]=[CH:36]3)=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:11][CH2:12][CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])([CH3:7])([CH3:6])[CH3:5].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[C:4]([O:8][C:9](=[O:41])[N:10]([CH2:22][CH2:23][CH2:24][N:25]([CH2:26][C:27]1[C:40]2[C:35]([CH:34]=[C:33]3[C:28]=1[CH:29]=[CH:30][CH:31]=[CH:32]3)=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:1][CH3:2])[CH2:11][CH2:12][CH2:13][NH:14][C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])([CH3:5])([CH3:6])[CH3:7]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 11720576{3-[(Anthracen-9-ylmethyl)-amino]-propyl}-(3-tert-butoxycarbonylamino-propyl)-carbamic acid tert-butyl ester

Produkt 1

HCID 11497655[3-(Anthracen-9-ylmethyl-ethyl-amino)-propyl]-(3-tert-butoxycarbonylamino-propyl)-carbamic acid tert-butyl esterAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

Ethylbromide (EtBr, 508 mg, 4.66 mmol) was dissolved in anhydrous acetonitrile and added to a stirring mixture of compound 10 (805 mg, 1.55 mmol) and anhydrous K2CO3 (644 mg, 4.66 mmol). The mixture was then stirred overnight at 75° C. under a N2 atmosphere. After the confirmation of the disappearance of the 10 by TLC, the solution was concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (20 mL) and washed three times with aqueous sodium carbonate. The organic layer was separated, dried with anhydrous Na2SO4, filtered and concentrated under vacuum. Flash column chromatography of the residue gave 11 as a light yellow oil. Yield 80%; Rf=0.35 (3% MeOH/CHCl3); 1H NMR (CDCl3) δ 8.43 (d, 2H), 8.25 (s, 1H), 7.86 (d, 2H), 7.43 (m, 2H), 7.37 (m, 2H), 4.34 (s, 2H), 2.78-2.92 (m, 4H), 2.64 (m, 4H), 2.36 (m, 2H), 1.21-1.48 (m, 23H), 1.16 (m, 2H); 13C NMR (CDCl3) δ 155.7, 131.1 (3C), 131.0, 128.7 (2C), 127.0 (2C), 125.2 (2C), 124.8 (2C), 124.5 (2C), 78.9, 78.4, 53.4, 50.6, 50.0, 47.9, 45.3, 43.5, 37.1, 28.3 (6C), 26.5, 11.7. HRMS (FAB) m/z calcd. for C33H47N3O4 (M+H)+ 550.3639, found 550.3619.

Aufarbeitung

  1. concentrationAfter the confirmation of the disappearance of the 10 by TLC, the solution was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in CH2Cl2 (20 mL)
  3. washwashed three times with aqueous sodium carbonate
  4. customThe organic layer was separated
  5. dry with materialdried with anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a36cc7035a194b5b81c93cb9fe910fe6
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07728041B2

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