Triethylamine → HCID 23447909, compound

HRID 1840300Notes

Reaction equation

HRID 1840300 reaction equation
[CH2:1]([C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]=1[C:14]([OH:16])=O)[CH3:2].Cl.[Cl:18][CH2:19][CH2:20][CH2:21][NH2:22].C(P(=O)(OCC)OCC)#N.C(N(CC)CC)C>CN(C)C=O.O>[Cl:18][CH2:19][CH2:20][CH2:21][NH:22][C:14]([C:4]1[C:5]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:6][O:7][C:3]=1[CH2:1][CH3:2])=[O:16]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 114690951-Propanamine, 3-chloro-, hydrochlorideHCID 135451045-Ethyl-3-phenyl-1,2-oxazole-4-carboxylic acid

Product 1

HCID 23447909HCID 23447909, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3.1 g of 5-ethyl-3-phenylisoxazole-4-carboxylic acid (prepared as described in J. Org. Chem. 1985, 50, 5660-5666), 2.94 g of 3-chloropropylamine hydrochloride, 2.62 mL of 92% diethyl cyanoposphonate and 4.38 mL of triethylamine in 50 mL of anhydrous dimethylformamide was stirred at room temperature for 3 hours, poured into 500 mL of water and extracted with ethyl acetate (2×200 mL). The combined organic layers were washed with water, dried (sodium sulphate) and the solvent was evaporated under vacuum. The crude was purified by flash chromatography (ethyl acetate-petroleum ether 3:7) to give 3.35 g (73%) of the title compound. M.p. 75-76° C.

Workup

  1. extractionextracted with ethyl acetate (2×200 mL)
  2. washThe combined organic layers were washed with water
  3. dry with materialdried (sodium sulphate)
  4. customthe solvent was evaporated under vacuum
  5. customThe crude was purified by flash chromatography (ethyl acetate-petroleum ether 3:7)

Sources & evidence

ORD record
ord-47e3b4f2a1a04753ad36ad04d5a8784f
Source dataset
uspto-grants-2004_01
Patent number
US06680319B2

Reaction notes

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