1-(2,6,6-Trimethylcyclohex-3-en-1-yl)but-2-en-1-one → Methyl 2-(4-oxo-4-(2,6,6-trimethylcyclohex-3-enyl)butan-2-ylamino)-3-(4-oxo-4-(2,6,6-trimethylcyclohex-3-enyl)butan-2-ylthio)propanoate

HRID 2260934

Reaktionsgleichung

Reaktionsgleichung von HRID 2260934
[CH3:1][CH:2]1[CH:7]=[CH:6][CH2:5][C:4]([CH3:9])([CH3:8])[CH:3]1[C:10](=[O:14])[CH:11]=[CH:12][CH3:13].C(N([CH:21]([CH3:23])[CH3:22])C(C)C)C.Cl.[CH3:25][O:26][C:27](=[O:32])[C@H:28]([CH2:30][SH:31])[NH2:29]>CO>[O:14]=[C:10]([CH:3]1[C:4]([CH3:8])([CH3:9])[CH2:5][CH:6]=[CH:7][CH:2]1[CH3:1])[CH2:11][CH:12]([NH:29][CH:28]([CH2:30][S:31][CH:12]([CH2:11][C:10](=[O:14])[CH:3]1[C:4]([CH3:8])([CH3:9])[CH2:5][CH:6]=[CH:23][CH:21]1[CH3:22])[CH3:13])[C:27]([O:26][CH3:25])=[O:32])[CH3:13]

Komponenten

5

Edukt 3

HCID 422961-(2,6,6-Trimethylcyclohex-3-en-1-yl)but-2-en-1-oneHCID 81531DiisopropylethylamineHCID 2733208L-Cysteine, methyl ester, hydrochloride

Produkt 1

HCID 68635878Methyl 2-(4-oxo-4-(2,6,6-trimethylcyclohex-3-enyl)butan-2-ylamino)-3-(4-oxo-4-(2,6,6-trimethylcyclohex-3-enyl)butan-2-ylthio)propanoateAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 1-(2,6,6-trimethylcyclohex-3-enyl)but-2-en-1-one (19.28 g, 100 mmol, 2 equiv.), ethyl diisopropylamine (6.45 g, 50 mmol, 1 equiv.) and L-Cystein methyl ester hydrochloride (8.60 g, 50 mmol, 1 equiv.) in MeOH (120 ml) is heated to reflux during 28 h. The solvent is removed in vacuo and the residue dissolved in methyl t-butyl ether. The solution is washed with dilute aq. NaCl, dried over MgSO4 and concentrated. The residue is purified by chromatography on SiO2 to yield 21.3 g (82%) of the title compound as yellowish, viscous oil.

Aufarbeitung

  1. temperatureto reflux during 28 h
  2. customThe solvent is removed in vacuo
  3. dissolutionthe residue dissolved in methyl t-butyl ether
  4. washThe solution is washed with dilute aq. NaCl
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue is purified by chromatography on SiO2

Quellen und Nachweise

ORD-Eintrag
ord-c9b7ced433ec4f2986752cd133d4161c
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07846887B2

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