Trifluoroacetic acid → HCID 57657992, compound

HRID 1670845Notes

Reaction equation

HRID 1670845 reaction equation
C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:6][CH:7]1[CH2:12][CH2:11][N:10]([CH:13]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[C:24]([Cl:25])=[CH:23][C:22]([C:26]4[CH:31]=[CH:30][C:29]([C:32]([N:34]5[CH2:39][CH2:38][CH:37]([C:40]([F:43])([F:42])[F:41])[CH2:36][CH2:35]5)=[O:33])=[CH:28][CH:27]=4)=[CH:21][C:20]=3[Cl:44])[C:14]2=[O:45])[CH2:9][CH2:8]1)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+]>C1COCC1.O.C(OCC)(=O)C>[Cl:44][C:20]1[CH:21]=[C:22]([C:26]2[CH:27]=[CH:28][C:29]([C:32]([N:34]3[CH2:39][CH2:38][CH:37]([C:40]([F:43])([F:41])[F:42])[CH2:36][CH2:35]3)=[O:33])=[CH:30][CH:31]=2)[CH:23]=[C:24]([Cl:25])[C:19]=1[CH2:18][N:15]1[CH2:16][CH2:17][CH:13]([N:10]2[CH2:11][CH2:12][CH:7]([OH:6])[CH2:8][CH2:9]2)[C:14]1=[O:45]

Participants

7

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 67354732HCID 67354732, compound

Product 1

HCID 57657992HCID 57657992, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Treat a mixture of 3-[4-(tert-butyl-diphenyl-silanyloxy)-piperidin-1-yl]-1-[3,5-dichloro-4′-(4-trifluoromethyl-piperidine-1-carbonyl)-biphenyl-4-ylmethyl]-pyrrolidin-2-one (0.25 g, 0.299 mmol) in THF (10 mL) and water (5 mL) with trifluoroacetic acid (5 mL), heat to reflux, and stir for 4 hours under N2. Cool the reaction and basify with 5N NaOH. Dilute the mixture with ethyl acetate and wash with water. Dry the organic layer (Na2SO4) and remove the solvent in vacuo to afford crude product. Purify with a 5 to 10% methanol in CH2Cl2 gradient to afford 0.078 g (44%) of the titled product. Rf=0.34 (9/1 CH2Cl2/methanol). ES MS (m/z): 598 (M+).

Workup

  1. additionTreat
  2. temperatureheat
  3. temperatureto reflux
  4. temperatureCool
  5. customthe reaction
  6. washwash with water
  7. dry with materialDry the organic layer (Na2SO4)
  8. customremove the solvent in vacuo
  9. customto afford crude product
  10. customPurify with a 5 to 10% methanol in CH2Cl2 gradient

Sources & evidence

ORD record
ord-50b96bfd58b54639b37d42c727fc072e
Source dataset
uspto-grants-2011_08
Patent number
US07994176B2

Reaction notes

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