Trifluoroacetic acid → HCID 59299302, compound

HRID 2235263Notes

Reaction equation

HRID 2235263 reaction equation
C([O:5][C:6]([C:8]1[CH:9]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH:21]3[CH2:25][CH2:24][N:23]([CH:26]4[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]4)[C:22]3=[O:32])=[C:16]([Cl:33])[CH:15]=2)[CH:11]=[CH:12][CH:13]=1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:33][C:16]1[CH:15]=[C:14]([C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([C:6]([OH:7])=[O:5])[CH:9]=2)[CH:19]=[CH:18][C:17]=1[CH2:20][CH:21]1[CH2:25][CH2:24][N:23]([CH:26]2[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]2)[C:22]1=[O:32]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59299462HCID 59299462, compound

Product 1

HCID 59299302HCID 59299302, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 3′-chloro-4′-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-biphenyl-3-carboxylic acid tert-butyl ester (Preparation 82) (506 mg, 1.08 mmol) in methylene chloride (5 mL). Add trifluoroacetic acid (5 mL) and stir at room temperature for 1 hour. Concentrate and redissolve in methylene chloride. Pour into 1N NaOH. Extract with ether. Acidify aqueous phase to pH 1. Extract with ether. Dry over sodium sulfate, filter and concentrate to yield 420 mg (94%) of the title compound as a white solid. Mass spectrum (apci) m/z=410.3

Workup

  1. concentrationConcentrate
  2. dissolutionredissolve in methylene chloride
  3. additionPour into 1N NaOH
  4. extractionExtract with ether
  5. extractionExtract with ether
  6. dry with materialDry over sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-9b6a8d1e18684202ba2650d1785d07ef
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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