Dicyclohexylcarbodiimide → HCID 67874023, Verbindung

HRID 1418692Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1418692
[CH3:1][C:2]([NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])([CH3:6])[C:3]([OH:5])=[O:4].C1(N=C=NC2CCCCC2)CCCCC1.O[CH:31]([C:34]1[CH:50]=[C:49]2[N:37]([CH2:38][C:39]3[C:40]2=[N:41][C:42]2[C:47]([CH:48]=3)=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36](=[O:51])[C:35]=1[CH3:52])[CH2:32][CH3:33]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:52][C:35]1[C:36](=[O:51])[N:37]2[C:49](=[CH:50][C:34]=1[CH:31]([O:4][C:3](=[O:5])[C:2]([NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])([CH3:1])[CH3:6])[CH2:32][CH3:33])[C:40]1=[N:41][C:42]3[C:47]([CH:48]=[C:39]1[CH2:38]2)=[CH:46][CH:45]=[CH:44][CH:43]=3

Komponenten

6

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 613105HCID 613105, VerbindungHCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanine

Produkt 1

HCID 67874023HCID 67874023, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a mixture containing 2-methyl-2-[N-[(1,1-dimethylethoxy)carbonyl]amino]propionic acid (406 mg, 2.0 mmol) and dicyclohexylcarbodiimide (432 mg, 2.0 mmol) in CH2Cl2 (3 mL) under an argon atmosphere were added (±)-7-(1-hydroxypropyl)-8-methylindolizino[1,2-b]quinolin-9(11H)-one (153 mg, 0.5 mmol) and 4-dimethylaminopyridine (25 mg). The resulting mixture was allowed to stir at room temperature for 4 d and then was poured into CH2Cl2, washed successively with 5% aqueous NaHCO3, 0.5N HCl and H2O, and dried over sodium sulfate. Removal of the solvent in vacuo and purification of the residue by column chromatography (silica gel) eluting with a solvent gradient of 1.5-5% MeOH/CH2Cl2 afforded the title compound as an off-white solid. 1H NMR (CDCl3) d 8.33 (s, 1H), 8.20 (d, J=8.9 Hz, 1H), 7.90 (d, J=8.3 Hz, 1H), 7.80 (m, 1H), 7.62 (m, 1H), 7.33 (s, 1H), 5.92 (dd, J=7.5, 6.3 Hz, 1H), 5.25 (s, 2H), 5.10 (br s, 1H), 2.38 (s, 3H), 2.08-1.82 (m, 2H), 1.56 (s, 3H), 1.55 (s, 3H), 1.41 (s, 9H), 0.99 (t, J=7.4 Hz, 3H).

Aufarbeitung

  1. washwashed successively with 5% aqueous NaHCO3, 0.5N HCl and H2O
  2. dry with materialdried over sodium sulfate
  3. customRemoval of the solvent
  4. customin vacuo and purification of the residue by column chromatography (silica gel)
  5. washeluting with a solvent gradient of 1.5-5% MeOH/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-fb84cae122dc46eda2d56ca6b666ec51
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05883255

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