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Triethylamine → cis-2-[N-(2,3-Dimethoxy-7-nitro-quinoxalin-5-ylmethyl)amino]-cyclohexane-1-carboxylic acid

HRID 1422253
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1422253
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[C:8]([OH:10])=[O:9].C(N(CC)CC)C.[CH3:18][O:19][C:20]1[C:29]([O:30][CH3:31])=[N:28][C:27]2[C:26]([CH:32]=O)=[CH:25][C:24]([N+:34]([O-:36])=[O:35])=[CH:23][C:22]=2[N:21]=1.S([O-])([O-])(=O)=O.[Na+].[Na+].[BH4-].[Na+]>ClCCl.C(O)C>[CH3:18][O:19][C:20]1[C:29]([O:30][CH3:31])=[N:28][C:27]2[C:22](=[CH:23][C:24]([N+:34]([O-:36])=[O:35])=[CH:25][C:26]=2[CH2:32][NH:1][C@H:2]2[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]2[C:8]([OH:10])=[O:9])[N:21]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 24436Sodium SulfateHCID 2724639(1R,2S)-2-Aminocyclohexane-1-carboxylic acidHCID 4311764Sodium borohydrideHCID 232979852,3-Dimethoxy-7-nitroquinoxaline-5-carbaldehyde

Produkt 1

HCID 53824769
cis-2-[N-(2,3-Dimethoxy-7-nitro-quinoxalin-5-ylmethyl)amino]-cyclohexane-1-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

105 mg (0.588 mmol) of cis-2-amino-cyclohexanecarboxylic acid and 82 μl (0.588 mmol) of triethylamine are added in succession to a solution of 129 mg (0.490 mmol) of 2,3-dimethoxy-7-nitro-quinoxaline-5-carbaldehyde in 1 ml of dichloromethane and 2 ml of ethanol. After 3 hours' stirring at room temperature, 1 g of anhydrous sodium sulfate is added to the suspension and the mixture is stirred for a further 20 hours at room temperature. The thick suspension is diluted with 0.5 ml of ethanol and 46 mg (1.23 mmol) of sodium borohydride are added. After 3 hours' stirring, there are added 0.5 ml of acetone and 10 minutes later 0.3 ml of acetic acid and filtration is carried out. The filter residue is washed with ethanol and dichloromethane. The filtrate is chromatographed on silica gel first with dichloromethane/ethyl acetate (97:3) and then with dichloromethane/methanol/glacial acetic acid (90:9:1). The title compound is obtained in the form of a white powder.

Aufarbeitung

  1. stirringthe mixture is stirred for a further 20 hours at room temperature
  2. additionare added
  3. stirringAfter 3 hours' stirring
  4. additionthere are added
  5. filtration0.5 ml of acetone and 10 minutes later 0.3 ml of acetic acid and filtration
  6. washThe filter residue is washed with ethanol and dichloromethane
  7. customThe filtrate is chromatographed on silica gel first with dichloromethane/ethyl acetate (97:3)

Quellen und Nachweise

ORD-Eintrag
ord-1ff17da756e74f698b0149766303ed75
Quelldatensatz
uspto-grants-2000_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06080743

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