1-(2,6,6-Trimethylcyclohex-3-en-1-yl)but-2-en-1-one → HCID 68635470, compound

HRID 2260935Notes

Reaction equation

HRID 2260935 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.[CH2:25]([O:27][C:28](=[O:33])[C@H:29]([CH2:31][SH:32])[NH2:30])[CH3:26]>CCO>[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:30][CH:29]([CH2:31][S:32][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:28]([O:27][CH2:25][CH3:26])=[O:33])[CH3:13]

Participants

5

Reactant 3

HCID 422961-(2,6,6-Trimethylcyclohex-3-en-1-yl)but-2-en-1-oneHCID 81531DiisopropylethylamineHCID 2723617Ethyl cysteinate hydrochloride

Product 1

HCID 68635470HCID 68635470, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-(2,6,6-trimethylcyclohex-3-enyl)but-2-en-1-one (83.0 g, 0.50 mol, 2 equiv.), ethyl diisopropylamine (32.3 g, 0.25 mol, 1 equiv.) and L-Cystein ethyl ester hydrochloride (46.5 g, 0.25 mol, 1 equiv.) in EtOH (600 ml) is heated to 60° C. during 44 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 85.5 g (71%) of the title compound as orange oil.

Workup

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

Sources & evidence

ORD record
ord-dc337b6f740e46d58b97be5ced8deaf8
Source dataset
uspto-grants-2010_12
Patent number
US07846887B2

Reaction notes

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