Triethylamine → HCID 19751537, compound

HRID 483809Notes

Reaction equation

HRID 483809 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=[O:20])[C:11](=[C:15]3[S:19][CH:18]=[CH:17][S:16]3)[C:12]([OH:14])=O)=[CH:9][C:4]=2[O:3][CH2:2]1.C(N(CC)CC)C.Cl.[NH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>CN(C)C=O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=[O:20])[C:11](=[C:15]3[S:19][CH:18]=[CH:17][S:16]3)[C:12]([NH:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[O:14])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 199401P,P-Diphenylphosphinic azideHCID 19751534HCID 19751534, compound

Product 1

HCID 19751537HCID 19751537, compoundYield 20.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolved in 15.0 ml of N,N-dimethylformamide were 959 mg of 3-(1,3-benzodioxol-5-yl)-2-(1,3-dithiol-2-ylidene)-3-oxopropionic acid and 997 μl of triethylamine, followed by the addition of 469 mg of methyl glycinate hydrochloride. The reaction mixture was ice-cooled, to which 737 μl of diphenylphosphoryl azide were added. The resulting mixture was stirred for 3 hours and, while allowing its temperature to rise to room temperature, was stirred overnight. The reaction mixture was extracted with ethyl acetate. The resulting organic layer was washed with water, shaken together with a saturated aqueous NaCl solution and then dried over anhydrous sodium sulfate. The solvent was distilled off, whereby crude oil was obtained. The oil was purified by column chromatography (silica gel: "Fuji Davidson BW-300", column: 35 mm across×190 mm long, N2 pressure: 0.3 kg/cm2, developer: ethyl acetate:n-hexane=3:2) and then recrystallized from a mixed solvent of ethyl acetate and n-hexane, whereby 247 mg of methyl N-[3-(1,3-benzodioxol-5-yl)-2-(1,3-dithiol-2-ylidene)-3-oxopropionyl]glycinate were obtained as yellow crystals (yield: 21.6%).

Workup

  1. additionwere added
  2. customto rise to room temperature
  3. stirringwas stirred overnight
  4. extractionThe reaction mixture was extracted with ethyl acetate
  5. washThe resulting organic layer was washed with water
  6. stirringshaken together with a saturated aqueous NaCl solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off
  9. customwhereby crude oil was obtained
  10. customThe oil was purified by column chromatography (silica gel
  11. custom"Fuji Davidson BW-300", column: 35 mm across×190 mm long, N2 pressure: 0.3 kg/cm2, developer: ethyl acetate:n-hexane=3:2) and then recrystallized from a mixed solvent of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-af7e9b1f4e2b45b780995aab29e47648
Source dataset
uspto-grants-1993_07
Patent number
US05227398

Reaction notes

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