Hydrochloric Acid → HCID 59410065, compound

HRID 1805155Notes

Reaction equation

HRID 1805155 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.[F:15][C:16]1([F:24])[CH2:20][NH:19][C@H:18]([C:21]([OH:23])=[O:22])[CH2:17]1.C(=O)([O-])[O-].[Na+].[Na+].Cl>O.O.C(O)C>[F:15][C:16]1([F:24])[CH2:20][N:19]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=2)[C@H:18]([C:21]([OH:23])=[O:22])[CH2:17]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 2230945-Fluoro-2-nitrobenzotrifluorideHCID 152161024,4-Difluoroproline

Product 1

HCID 59410065HCID 59410065, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19096565Water ethanolSolvent

Conditions

Temperature
90 °C

Procedure

To 4-fluoro-1-nitro-2-(trifluoromethyl)benzene (416 mg, 2 mmol), (S)-4,4-difluoropyrrolidine-2-carboxylic acid (301 mg, 2 mmol), and sodium carbonate (633 mg, 574 μL, 6.0 mmol) was added 1:1 water/Ethanol (8 mL) and the reaction mixture was heated at 90° C. for 72 h. The reaction mixture was diluted with water (50 mL) then acidified with 1 N HCl and the product was extracted with ethyl acetate. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to yield (S)-4,4-difluoro-1-(4-nitro-3-(trifluoromethyl)phenyl)pyrrolidine-2-carboxylic acid as a brown oil (600 mg, 89%), which was used directly in the next reaction. LC/MS: m/z 341.00 (M+H)+ at 1.49 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-17b903303faa41ff8cad93aff20327da
Source dataset
uspto-grants-2013_01
Patent number
US08354427B2

Reaction notes

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