Triethylamine → HCID 58307494, compound

HRID 222794Notes

Reaction equation

HRID 222794 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11](O)=[CH:10][C:9](=[O:13])[N:8]([CH2:14][CH2:15][CH3:16])[C:7]=1[CH3:17])=[O:5])[CH3:2].P(Cl)(Cl)([Cl:20])=O.C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:11]([Cl:20])=[CH:10][C:9](=[O:13])[N:8]([CH2:14][CH2:15][CH3:16])[C:7]=1[CH3:17])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 58307485HCID 58307485, compound

Product 1

HCID 58307494HCID 58307494, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-hydroxy-2-methyl-6-oxo-1-propyl-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester (2.00 g, 8.36 mmol) and phosphoryl chloride (4.67 mL, 50.2 mmol), triethylamine (1.16 mL, 8.36 mmol) and methylene chloride (2 mL) were added and the mixture was stirred at r.t. overnight. It was concentrated in vacuo, poured into ice and carefully neutralised with sat.aq. K2CO3 solution. It was extracted with ethyl acetate (3×300 mL), the combined organic solution was washed with brine (20 mL), dried (MgSO4) and evaporated. The title compound was purified by flash chromatography, yield 0.6 g, 30%. LC-MS (m/z) 258.5 (MH+); tR=1.21 (method C).

Workup

  1. additionwere added
  2. concentrationIt was concentrated in vacuo
  3. additionpoured into ice
  4. extractionIt was extracted with ethyl acetate (3×300 mL)
  5. washthe combined organic solution was washed with brine (20 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe title compound was purified by flash chromatography, yield 0.6 g, 30%

Sources & evidence

ORD record
ord-220a9814571146d4901f78c7345d066c
Source dataset
uspto-grants-2012_06
Patent number
US08207347B2

Reaction notes

Loading…