Triethylamine → HCID 54115290, compound

HRID 1271458Notes

Reaction equation

HRID 1271458 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=[O:5])#[N:2].[C:7](Cl)(=O)C(Cl)=O.[F:13][C:14](=[CH:17][CH2:18]C)[CH2:15]O.C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[C:1]([CH2:3][C:4]([O:6][CH2:15][C:14]([F:13])=[C:17]([CH3:18])[CH3:7])=[O:5])#[N:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9740Cyanoacetic acidHCID 65578Oxalyl chlorideHCID 53829981HCID 53829981, compound

Product 1

HCID 54115290HCID 54115290, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of cyano acetic acid (2.25 g, 26.4 mmol) in 30 mL dry CH2Cl2 was cooled in ice water before 2.3 mL (26.4 mmol) of oxalyl chloride and 3 drops of DMF were added. The mixture was warmed to room temperature with stirring overnight before being added dropwise to an ice-cooled solution of 2.5 g (24 mmol) of 2-fluoro-4-methyl-2-buten-1-ol (Cane, D. E.; Yang, G.; Xue, Q.; Shin, J. H. Biochemistry (1995), 3418, 2471–9) and 3.7 mL (26.4 mmol) triethylamine. After stirring 3 h at room temperature, solvent was removed and the residue was partitioned between water and ether. The ether layer was separated and washed with brine. The combined aqueous washings were extracted with ether which was washed with brine. The combined ether extracts were dried (MgSO4), and solvent was removed to afford 3.5 g of the title compound of Step A as an oil, 1H NMR (CDCl3) δ 1.7 (m, 6H), 3.5 (s, 2H), 4.85 (d, J=22 Hz, 2H).

Workup

  1. additionwere added
  2. stirringAfter stirring 3 h at room temperature
  3. customsolvent was removed
  4. customthe residue was partitioned between water and ether
  5. customThe ether layer was separated
  6. washwashed with brine
  7. extractionThe combined aqueous washings were extracted with ether which
  8. washwas washed with brine
  9. dry with materialThe combined ether extracts were dried (MgSO4), and solvent
  10. customwas removed

Sources & evidence

ORD record
ord-41f6432a978643a5b3c2b5335e1d3b34
Source dataset
uspto-grants-2007_04
Patent number
US07205331B2

Reaction notes

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