Triethylamine → HCID 15021171, compound

HRID 1090012Notes

Reaction equation

HRID 1090012 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([CH2:13][C@@H:14]([C:16]([OH:18])=[O:17])[NH2:15])=[CH:6]2.S(Cl)(Cl)=O.[CH2:23](N(CC)CC)[CH3:24].[C:30]([O:34][C:35](ON=C(C1C=CC=CC=1)C#N)=[O:36])([CH3:33])([CH3:32])[CH3:31]>C(O)C.O.O1CCOCC1>[CH2:23]([O:17][C:16](=[O:18])[C@H:14]([CH2:13][C:7]1[CH:8]=[N:9][C:10]2[C:5]([CH:6]=1)=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[NH:15][C:35]([O:34][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:36])[CH3:24]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 15021169HCID 15021169, compound

Product 1

HCID 15021171HCID 15021171, compoundYield 73.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 0.54 g (2.19 mmol) of 3-(6-methoxy-3-quinolyl)alanine in 13.5 mL of ethanol was added dropwise 0.68 mL of thionyl chloride at 0° C. The reaction mixture was refluxed overnight, then was evaporated in vacuo. triturated with benzene and evaporated to dryness in vacuo. The crude product, 3-(6-methoxy-3-quinolyl)alanine ethyl ester dihydrochloride, was combined with 0.93 mL (6.4 mmol) of triethylamine and 14.2 mL of 50% aqueous 1,4-dioxane; to that mixture was added, in one portion, 0.58 g (2.4 mmol) of 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile. The resultant mixture was stirred overnight at room temperature, then was diluted with 15 mL of water and extracted twice with chloroform. The organic layer was washed with water, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel, using 5:1 methylene chloride/ethyl acetate as eluent, to give a white solid which was recrystallized from isopropyl ether to afford 0.6 g (73.3 %) of the title compound, melting at about 127° C. and having the structural formula: ##STR116## The identity of the product was confirmed by NMR and IR spectral analyses as well as by elemental analysis.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customwas evaporated in vacuo
  3. customtriturated with benzene
  4. customevaporated to dryness in vacuo
  5. extractionextracted twice with chloroform
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated in vacuo
  9. customThe residue was chromatographed on silica gel
  10. customto give a white solid which
  11. customwas recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-aa841ff366fa412bb4bf142d0ecccf5b
Source dataset
uspto-grants-1992_01
Patent number
US05079366

Reaction notes

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