Nitric Acid → 2,2,2-Trifluoro-N-[(1S,2R)-2-hydroxy-2-(4-hydroxy-3-nitrophenyl)-1-methylethyl]acetamide

HRID 2220595Notes

Reaction equation

HRID 2220595 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([NH:5][C@@H:6]([CH3:16])[C@H:7]([OH:15])[C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)=[O:4].[N+:19]([O-])([OH:21])=[O:20].C(OCC)(=O)C>C(O)(=O)C>[F:1][C:2]([F:17])([F:18])[C:3]([NH:5][C@@H:6]([CH3:16])[C@H:7]([OH:15])[C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([N+:19]([O-:21])=[O:20])[CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 8857Ethyl AcetateHCID 866117652,2,2-trifluoro-N-[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]acetamide

Product 1

HCID 866117642,2,2-Trifluoro-N-[(1S,2R)-2-hydroxy-2-(4-hydroxy-3-nitrophenyl)-1-methylethyl]acetamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2,2,2-trifluoro-N-[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]acetamide (26.9 g) in acetic acid (85 mL) was added dropwise 70% nitric acid (6.78 mL) at room temperature with stirring. The mixture was stirred for 15 minutes at that temperature. The resulting mixture was poured into ice-water (500 g), and ethyl acetate was added. The organic layer was separated, washed successively with saturated aqueous solution of sodium bicarbonate and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium-pressure liquid silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1) to afford the title compound (33.5 g).

Workup

  1. stirringThe mixture was stirred for 15 minutes at that temperature
  2. additionwas added
  3. customThe organic layer was separated
  4. washwashed successively with saturated aqueous solution of sodium bicarbonate and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by medium-pressure liquid silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-5791930fa1d747779f46a32650203adf
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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