Nitric Acid → HCID 19082109, compound

HRID 265303Notes

Reaction equation

HRID 265303 reaction equation
[N+:1]([O-:4])(O)=[O:2].[C:5]1([CH2:11][CH2:12][O:13][CH2:14][CH2:15][S:16]([CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])(=[O:18])=[O:17])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>FC(F)(F)C(O)=O.O>[CH3:24][O:23][C:21](=[O:22])[CH2:20][CH2:19][S:16]([CH2:15][CH2:14][O:13][CH2:12][CH2:11][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=1[N+:1]([O-:4])=[O:2])(=[O:17])=[O:18]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 19082203HCID 19082203, compound

Product 1

HCID 19082109HCID 19082109, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Concentrated nitric acid (3.25 ml) was added dropwise over a half hour period to a stirred cooled (ice/salt) solution of methyl 3-[2-[2-phenylethoxy]ethylsulphonyl]propanoate (15.12 g) (prepared from the acid, which was itself prepared by the procedure outlined in Example 1b)) in trifluoroacetic acid. The reaction was allowed to warm to room temperature, stirred overnight, diluted with water and extracted several times with ethyl acetate. The combined organic extracts were washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to yield the crude mixture of isomeric methyl 3-[2-[2-[nitrophenyl]ethoxy]ethylsulphonyl propanoates. The subtitled compound was separated from the other isomers by normal phase preparative HPLC using 1:1 hexane:ethyl acetate as eluant.

Workup

  1. customprepared from the acid, which
  2. customprepared by the procedure
  3. extractionextracted several times with ethyl acetate
  4. washThe combined organic extracts were washed with water and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customto yield the crude
  8. customThe subtitled compound was separated from the other isomers by normal phase preparative HPLC

Sources & evidence

ORD record
ord-7ceae03751aa4d82ad90949a3802e7c5
Source dataset
uspto-grants-1997_07
Patent number
US05648370

Reaction notes

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