Oxalyl chloride → HCID 19422059, compound

HRID 744693Notes

Reaction equation

HRID 744693 reaction equation
[O:1]=[C:2]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=O.C(Cl)(=O)C(Cl)=O.Cl.[CH3:26][NH:27][O:28][CH3:29].C(=O)(O)[O-].[Na+]>N1C=CC=CC=1.CN(C)C=O.O1CCCC1>[O:9]=[C:7]([N:27]([O:28][CH3:29])[CH3:26])[CH2:6][CH2:5][CH2:4][CH2:3][C:2]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)=[O:1]

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 19422065HCID 19422065, compound

Product 1

HCID 19422059HCID 19422059, compoundYield 22.3%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

6-Oxo-6-(4-methoxyphenylamino)hexanoic acid (509 mg), tetrahydrofuran (12 mL) and dimethylformamide (0.1 mL) were cooled 0°-5° Oxalyl chloride (0.23 mL) was added and the reaction was allowed to stir for fifteen minutes before the addition of N,O-dimethylhydroxylamine hydrochloride (221 mg). After twenty minutes, pyridine (0.8 mL) was added and reaction was warmed to 20°-25° C. Saturated sodium bicarbonate solution (100 mL) was added and the reaction was extracted with dichloromethane (2×30 mL). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo to afford a brown oil which was purified by chromatography eluting with 95:5 ethyl acetate:hexanes. The resulting white solid was recrystallized from ethyl acetate:hexanes to give the title compound as white crystals (133 mg).

Workup

  1. additionwas added
  2. waitAfter twenty minutes
  3. customreaction
  4. temperaturewas warmed to 20°-25° C
  5. extractionthe reaction was extracted with dichloromethane (2×30 mL)
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customto afford a brown oil which
  9. customwas purified by chromatography
  10. washeluting with 95:5 ethyl acetate
  11. customThe resulting white solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ba19267021f7433cb6b9dfd378cfcc7f
Source dataset
uspto-grants-1996_09
Patent number
US05559143

Reaction notes

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