Hydrochloric Acid → HCID 19422080, compound

HRID 273816Notes

Reaction equation

HRID 273816 reaction equation
[O:1]=[C:2](N(OC)C)[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)=[O:8].[CH2:22]([Mg]Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl>O1CCCC1>[CH3:17][O:16][C:13]1[CH:12]=[CH:11][C:10]([NH:9][C:7](=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][C:2](=[O:1])[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 19422059HCID 19422059, compoundHCID 178418336HCID 178418336, compound2×

Product 1

HCID 19422080HCID 19422080, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

6-Oxo-6-(N,O-dimethylhydroxylamino)-N-(4-methoxyphenyl) hexanamide (454 mg) was dissolved in tetrahydrofuran (13 mL) and cooled to -78° C. Benzylmagnesium chloride in tetrahydrofuran (2.0M, 1.6 mL) was added and reaction was warmed to 20° C. After 24 hours, additional benzylmagnesium chloride in tetrahydrofuran (2.0M, 0.4 mL) was added. After 24 hours, 1.0M aqueous hydrochloric acid (10 mL) was added and reaction extracted using dichloromethane (2×15 mL). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo. The resulting solid was chromatographed eluting with 30:70 ethyl acetate:hexanes to afford the title compound (Rf of 0.68 in 70:30 ethyl acetate:hexanes) as white crystals (200 mg).

Workup

  1. customreaction
  2. temperaturewas warmed to 20° C
  3. waitAfter 24 hours
  4. customreaction
  5. extractionextracted
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe resulting solid was chromatographed
  9. washeluting with 30:70 ethyl acetate

Sources & evidence

ORD record
ord-92d86cc111a34a7fb59a459346345aa2
Source dataset
uspto-grants-1995_02
Patent number
US05387604

Reaction notes

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