Water → HCID 66905198, compound

HRID 1692109Notes

Reaction equation

HRID 1692109 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][C@@H:27]3[CH2:31][CH2:30][N:29]([N:32]4[CH2:37][CH2:36][CH:35]([O:38][Si](C(C)C)(C(C)C)C(C)C)[CH2:34][CH2:33]4)[C:28]3=[O:49])=[CH:22][CH:21]=2)[CH:5]=[CH:6][C:7]=1[C:8]([N:10]1[CH2:15][CH2:14][CH:13]([C:16]([F:19])([F:18])[F:17])[CH2:12][CH2:11]1)=[O:9].C1COCC1.O.C(O)(C(F)(F)F)=O>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:20]2[CH:21]=[CH:22][C:23]([CH2:26][C@@H:27]3[CH2:31][CH2:30][N:29]([N:32]4[CH2:33][CH2:34][CH:35]([OH:38])[CH2:36][CH2:37]4)[C:28]3=[O:49])=[CH:24][CH:25]=2)[CH:5]=[CH:6][C:7]=1[C:8]([N:10]1[CH2:11][CH2:12][CH:13]([C:16]([F:18])([F:19])[F:17])[CH2:14][CH2:15]1)=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 8028TetrahydrofuranHCID 66905040HCID 66905040, compound

Product 1

HCID 66905198HCID 66905198, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Treat a mixture of (R)-3-[3′-chloro-4′-(4-trifluoromethyl-piperidine-1-carbonyl)-biphenyl-4-ylmethyl]-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-2-one (0.12 g), THF (3 mL) and water (3 mL) with TFA (1 mL) at room temperature for 5 hours. Dilute the reaction 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 100% ethyl acetate and 10% methanol in methylene chloride to afford 0.05 g (53%) of the titled product. MS (m/z): 564 (M+).

Workup

  1. additionTreat
  2. additionDilute
  3. washwash with sodium bicarbonate (sat.)
  4. dry with materialDry the organic layer (Na2SO4)
  5. customremove the solvent in vacuo
  6. customto afford crude product
  7. custompurify on silica gel column with 100% ethyl acetate and 10% methanol in methylene chloride

Sources & evidence

ORD record
ord-8492698c0a8d4f728d44627ca9c5b6d6
Source dataset
uspto-grants-2012_04
Patent number
US08153807B2

Reaction notes

Loading…