Potassium Carbonate → HCID 66671794, compound

HRID 1171161Notes

Reaction equation

HRID 1171161 reaction equation
FC(F)(F)[C:3]([OH:5])=O.[Cl:8][C:9]1[CH:10]=[C:11]([C:29]2[CH:34]=[CH:33][C:32]([C:35]([N:37]3[CH2:42][CH2:41][CH:40]([C:43]([F:46])([F:45])[F:44])[CH2:39][CH2:38]3)=[O:36])=[CH:31][CH:30]=2)[CH:12]=[C:13]([Cl:28])[C:14]=1[CH2:15][C@@H:16]1[CH2:20][CH2:19][N:18]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[C:17]1=[O:27].C(=O)([O-])[O-].[K+].[K+].C[Si]([N:57]=[C:58]=O)(C)C>CC(C)=O>[CH3:58][NH:57][C:3]([N:24]1[CH2:23][CH2:22][CH:21]([N:18]2[CH2:19][CH2:20][C@@H:16]([CH2:15][C:14]3[C:9]([Cl:8])=[CH:10][C:11]([C:29]4[CH:30]=[CH:31][C:32]([C:35]([N:37]5[CH2:38][CH2:39][CH:40]([C:43]([F:46])([F:44])[F:45])[CH2:41][CH2:42]5)=[O:36])=[CH:33][CH:34]=4)=[CH:12][C:13]=3[Cl:28])[C:17]2=[O:27])[CH2:26][CH2:25]1)=[O:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70696Trimethylsilyl isocyanateHCID 86629124HCID 86629124, compound

Product 1

HCID 66671794HCID 66671794, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of (R)-3-[3,5-Dichloro-4′-(4-trifluoromethyl-piperidine-1-carbonyl)-biphenyl-4-ylmethyl]-1-piperidin-4-yl-pyrrolidin-2-one trifluoroacetic acid (Preparation 30) (112 mg, 0.16 mmol) and potassium carbonate (40 mg, 0.32 mmol) in Acetone (5 mL) is treated with Trimethylsilyl-isocyanate (30 mg, 0.24 mmol). The reaction is stirred overnight at room temperature. The reaction is quenched with 1N HCl and extracted with Et2O. The organic is washed with brine, dried over MgSO4, and filtered. The crude is purified by silica gel column chromatography using Hexanes:EtOAc to elute pure product. The solvent is removed to afford 0.038 g (38%) of product. MS (m/e): 626 (M+1).

Workup

  1. customThe reaction is quenched with 1N HCl
  2. extractionextracted with Et2O
  3. washThe organic is washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe crude is purified by silica gel column chromatography
  7. washEtOAc to elute pure product
  8. customThe solvent is removed

Sources & evidence

ORD record
ord-9576fd558ef14a48a08ea25d09fe1478
Source dataset
uspto-grants-2010_11
Patent number
US07829582B2

Reaction notes

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