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

Reaction equation

HRID 2260934 reaction equation
[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]

Participants

5

Reactant 3

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

Product 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)propanoateYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c9b7ced433ec4f2986752cd133d4161c
Source dataset
uspto-grants-2010_12
Patent number
US07846887B2

Linked notes

Loading…