Nitric Acid → HCID 178475040, compound

HRID 35963Notes

Reaction equation

HRID 35963 reaction equation
C(OC(=O)C)(=O)C.[N+:8]([O-:11])([OH:10])=[O:9].[C:12]([NH:15][C@H:16]1[CH2:21][CH2:20][C@H:19](O)[CH2:18][CH2:17]1)(=[O:14])[CH3:13].C(=O)([O-])O.[Na+]>C(#N)C>[C:12]([NH:15][C@H:16]1[CH2:21][CH2:20][C@H:19]([O:9][N+:8]([O-:11])=[O:10])[CH2:18][CH2:17]1)(=[O:14])[CH3:13]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 178475038HCID 178475038, compound

Product 1

HCID 178475040HCID 178475040, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

28.3 ml (0.3 mol) acetic acid anhydride are mixed with 375 ml acetonitrile, cooled in an ice-bath to 0°-5° C. and 12.6 ml (0.3 mol) 100% nitric acid added dropwise. After 30 minutes, 15.7 g (0.1 mol) solid trans-N-acetyl-4-hydroxycyclohexylamine are added thereto with stirring and cooling at 0°-5° C. The reaction mixture is further stirred for 3 h at 0°-5° C. and subsequently allowed to flow carefully into a solution of 150 g (18 mol) sodium hydrogen carbonate in 500 ml ice water. After extraction with ethyl acetate, drying of the organic phase with sodium sulphate and distilling off in a vacuum, there remain 17.8 g of crude product. After recrystallisation from ethyl acetate, there are obtained 10.3 g of the title compound of the m.p. 146°-148° C., i.e. 50% of theory.

Workup

  1. temperaturecooled in an ice-bath to 0°-5° C.
  2. temperaturecooling at 0°-5° C
  3. stirringThe reaction mixture is further stirred for 3 h at 0°-5° C.
  4. extractionAfter extraction with ethyl acetate
  5. dry with materialdrying of the organic phase with sodium sulphate
  6. distillationdistilling off in a vacuum, there remain 17.8 g of crude product
  7. customAfter recrystallisation from ethyl acetate, there

Sources & evidence

ORD record
ord-5772ed044caa42808bd1e0d3d45fadff
Source dataset
uspto-grants-1995_05
Patent number
US05411989

Reaction notes

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