4-Methylmorpholine → 1,2,3,4-Tetrahydronaphthalene-2-carboxylic acid (2-amino-4,6-dioxo-3,5-dipropylcyclohex-1-enyl)amide

HRID 3657

Reaktionsgleichung

Reaktionsgleichung von HRID 3657
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[C:11]([OH:13])=O.C[N:15]1[CH2:20][CH2:19][O:18]CC1.ClC(O[CH2:25][CH:26](C)[CH3:27])=O.C(N1[C:39]([NH2:40])=[C:38](N)[C:36](=[O:37])N(CCC)C1=O)CC.O1[CH2:49][CH2:48][CH2:47][CH2:46]1>C(OCC)C>[NH2:40][C:39]1[CH:38]([CH2:25][CH2:26][CH3:27])[C:36](=[O:37])[CH:46]([CH2:47][CH2:48][CH3:49])[C:19](=[O:18])[C:20]=1[NH:15][C:11]([CH:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1]1)=[O:13]

Komponenten

7

Edukt 5

HCID 79724-MethylmorpholineHCID 8028TetrahydrofuranHCID 62365Isobutyl chloroformateHCID 1013701,2,3,4-Tetrahydro-2-naphthoic acidHCID 50986055,6-Diamino-1,3-dipropyl-2,4(1H,3H)-pyrimidinedione

Produkt 1

HCID 700716701,2,3,4-Tetrahydronaphthalene-2-carboxylic acid (2-amino-4,6-dioxo-3,5-dipropylcyclohex-1-enyl)amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Dissolve 1,2,3,4-tetrahydro-2-naphthoic acid (1.0 g, 5.67 mmol) in tetrahydrofuran (40 ml). Add N-methylmorpholine (0.62 ml, 5.67 mmol) and cool to -20° C. Add isobutyl chloroformate (0.73 ml, 5.67 mmol) and stir for 25 minutes. Then add 1,3-di-n-propyl-5,6-diaminouracil (1.28 g, 5.67 mmol, in 5 ml dimethylformamide) and stir the reaction for 5 hours at -20° C. Warm the reaction to room temperature and dilute with diethyl ether (300 ml). Separate the layers and rinse the organic layer with saturated sodium bicarbonate (200 ml), saturated sodium chloride solution (200 ml), dry over anhydrous magnesium sulfate, filter and concentrate. Purify the residue by radial chromatography (2% to 4% to 6% methanol/chloroform, 4 mm plate) to provide 1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (2-amino-4,6-dioxo-3,5-dipropylcyclohex-1-enyl)amide (2.0 g) as a foam.

Aufarbeitung

  1. customthe reaction for 5 hours at -20° C
  2. temperatureWarm
  3. customthe reaction to room temperature
  4. customSeparate the layers
  5. washrinse the organic layer with saturated sodium bicarbonate (200 ml), saturated sodium chloride solution (200 ml)
  6. dry with materialdry over anhydrous magnesium sulfate
  7. filtrationfilter
  8. concentrationconcentrate
  9. customPurify the residue by radial chromatography (2% to 4% to 6% methanol/chloroform, 4 mm plate)

Quellen und Nachweise

ORD-Eintrag
ord-0d42d3e8acbb4e3db3bb6bef4ab7f44e
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05734052

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