Triethylamine → (R)-2-Heptyl-pent-4-enoic acid dimethylamide

HRID 1275404Notes

Reaction equation

HRID 1275404 reaction equation
[CH2:1]([C@H:8]([CH2:12][CH:13]=[CH2:14])[C:9](O)=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].Cl.[CH3:16][NH:17][CH3:18].C(P(=O)(OCC)OCC)#N.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[CH3:16][N:17]([CH3:18])[C:9](=[O:10])[C@H:8]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[CH2:12][CH:13]=[CH2:14]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 76257Diethyl cyanophosphonateHCID 11041739(2R)-2-Heptyl-pent-4-enoic acid

Product 1

HCID 54259984(R)-2-Heptyl-pent-4-enoic acid dimethylamideYield 100.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 5.00 g (0.025 mol) of the product of Example 5 and 2.27 g (0.028 mol) of dimethylamine hydrochloride in DMF at 0° C. was added 4.2 mL (0.028 mol) of diethyl cyanophosphonate followed by 7.38 mL (0.053 mol) of triethylamine. The reaction mixture was stirred at 0 degrees for 1 h and then at room temperature for 3 h. The resulting pale yellow suspension was diluted with 750 mL of EtOAc/Hex (2:1) and this solution was then washed with 5% aqueous HCl solution, water, saturated sodium bicarbonate and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:4) to provide 5.68 g (100%) of the title compound as a colorless oil. CI Mass Spec: 226.3 (M+H).

Workup

  1. waitat room temperature for 3 h
  2. washthis solution was then washed with 5% aqueous HCl solution, water, saturated sodium bicarbonate and brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:4)

Sources & evidence

ORD record
ord-b3759146f281494786521db3a7c9c331
Source dataset
uspto-grants-2000_12
Patent number
US06160132

Reaction notes

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