Triethylamine → HCID 86743002, compound

HRID 1761778Notes

Reaction equation

HRID 1761778 reaction equation
[CH3:1]/[C:2](/[CH2:7][CH2:8]/[CH:9]=[C:10](\[CH3:18])/[CH2:11][CH2:12][C:13](=[O:17])[C:14]([CH3:16])=[CH2:15])=[CH:3]\[C:4]([NH2:6])=[O:5].[C:19]([O:23][CH3:24])(=[O:22])[CH2:20][SH:21].C(N(CC)CC)C>CO>[C:4](/[CH:3]=[C:2](\[CH3:1])/[CH2:7][CH2:8]/[CH:9]=[C:10](\[CH3:18])/[CH2:11][CH2:12][C:13](=[O:17])[CH:14]([CH3:16])[CH2:15][S:21][CH2:20][C:19]([O:23][CH3:24])=[O:22])(=[O:5])[NH2:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 16907Methyl ThioglycolateHCID 21242302HCID 21242302, compound

Product 1

HCID 86743002HCID 86743002, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.0 g (0.008 mol) of (E,E)-3,7,11-trimethyl-10-oxo-2,6,11-dodecatrienamide in 60 ml of methanol is treated with 2.3 ml of methyl thioglycolate and 3.4 ml of triethylamine. The solution is stirred at room temperature for 8 hours under argon. After removing the solvent the residue is taken up in water and methylene chloride. After extraction the organic phase is dried and freed from solvent. The residue is chromatographed on silica gel with ether-methanol 20:1. There is obtained methyl [[(6E,10E)-11-carbamoyl-2,6,10-trimethyl-3-oxo-6,10-undecadienyl]thio]acetate which exhibits the following absorption bands in the IR spectrum: 3447 cm-1, 3352 cm-1, 3195 cm-1, 1735 cm-1, 1712 cm-1, 1669 cm-1, 1638 cm-1 1609 cm-1, 1436 cm-1, 1300 cm-1, 1137 cm-1, 1008 cm-1.

Workup

  1. customAfter removing the solvent the residue
  2. extractionAfter extraction the organic phase
  3. customis dried
  4. customThe residue is chromatographed on silica gel with ether-methanol 20:1

Sources & evidence

ORD record
ord-2081bd5af06342748e7678260f1af569
Source dataset
uspto-grants-1989_05
Patent number
US04827004

Reaction notes

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