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

反応式

HRID 2260934 の反応式
[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]

参加物

5

反応物 3

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

生成物 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)propanoate収率 82%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c9b7ced433ec4f2986752cd133d4161c
出典データセット
uspto-grants-2010_12
特許番号
US07846887B2

関連ノート

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