Sulfuric Acid → HCID 178501905, compound

HRID 365112Notes

Reaction equation

HRID 365112 reaction equation
C1O[C:4]([CH:7]2[C:12](=[O:13])[CH:11]([CH3:14])[CH2:10][N:9]([C:15]([O:17][CH3:18])=[O:16])[CH2:8]2)([NH:5]O)[O:3]C1.OS(O)(=O)=O.[OH-].[Na+]>O>[OH:3][C:4]1[C:7]2[CH2:8][N:9]([C:15]([O:17][CH3:18])=[O:16])[CH2:10][CH:11]([CH3:14])[C:12]=2[O:13][N:5]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 56616876HCID 56616876, compound

Product 1

HCID 178501905HCID 178501905, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(RS)-1-Methoxycarbonyl-4-oxo-5-methylpiperidine-3-carbohydroxamic acid ethylene ketal (3.95 g; 14.4 mmol) was at 5° C. added in small portions to a mixture of 96% H2SO4 (9 ml) and water (1 ml). The mixture was then kept at 50° C. for 30 min. and poured on ice. The pH was adjusted to 3 with 9N sodium hydroxide and the mixture was extracted three times with methylene chloride (75 ml). Evaporation in vacuo yielded 2.23 g of crude product. To obtain an analytically pure sample the crude product was purified by CC (eluent: ethyl acetate containing 2% methanol and 2% glacial acetic acid). Recrystallization from toluene yielded the pure title compound, M.P. 128°-129° C.

Workup

  1. customwas at 5° C.
  2. additionpoured on ice
  3. extractionthe mixture was extracted three times with methylene chloride (75 ml)
  4. customEvaporation in vacuo
  5. customyielded 2.23 g of crude product
  6. customTo obtain an analytically pure sample the crude product
  7. customwas purified by CC (eluent: ethyl acetate containing 2% methanol and 2% glacial acetic acid)
  8. customRecrystallization from toluene

Sources & evidence

ORD record
ord-4af2007892bf45439958a30d1cc08bdb
Source dataset
uspto-grants-1986_08
Patent number
US04608378

Reaction notes

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