Water → HCID 57657996, compound

HRID 1670840Notes

Reaction equation

HRID 1670840 reaction equation
C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:6][CH:7]1[CH2:12][CH2:11][CH: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.C1COCC1.O.C(O)(C(F)(F)F)=O>C(OCC)(=O)C>[Cl:44][C:20]1[CH:21]=[C:22]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([N:34]3[CH2:35][CH2:36][CH:37]([C:40]([F:42])([F:41])[F:43])[CH2:38][CH2:39]3)=[O:33])=[CH:28][CH:27]=2)[CH:23]=[C:24]([Cl:25])[C:19]=1[CH2:18][N:15]1[CH2:16][CH2:17][CH:13]([CH:10]2[CH2:11][CH2:12][CH:7]([OH:6])[CH2:8][CH2:9]2)[C:14]1=[O:45]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 8028TetrahydrofuranHCID 67354701HCID 67354701, compound

Product 1

HCID 57657996HCID 57657996, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Treat a mixture of 3-[4-(tert-butyl-diphenyl-silanyloxy)-cyclohexyl]-1-[3,5-dichloro-4′-(4-trifluoromethyl-piperidine-1-carbonyl)-biphenyl-4-ylmethyl]-pyrrolidin-2-one (0.18 g), THF (6 mL) and water (6 mL) with TFA (2 mL) at room temperature for 1 hour and then at 55° C. for 12 hours. Cool the reaction, dilute with ethyl acetate, and wash with sodium bicarbonate (sat.). Dry the organic layer (Na2SO4), remove the solvent in vacuo to afford crude product, and purify on silica gel column with 50% ethyl acetate in hexanes to 100% ethyl acetate gradient to afford 0.075 g (59%) of the titled product. MS (m/z): 599 (M+).

Workup

  1. additionTreat
  2. temperatureCool
  3. customthe reaction
  4. washwash with sodium bicarbonate (sat.)
  5. dry with materialDry the organic layer (Na2SO4)
  6. customremove the solvent in vacuo
  7. customto afford crude product
  8. custompurify on silica gel column with 50% ethyl acetate in hexanes to 100% ethyl acetate gradient

Sources & evidence

ORD record
ord-12c9a77fb07443fea559d72d12484070
Source dataset
uspto-grants-2011_08
Patent number
US07994176B2

Reaction notes

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