Potassium Carbonate → HCID 59299359, compound

HRID 2235287Notes

Reaction equation

HRID 2235287 reaction equation
[N+](C1C=CC(C([O:10][CH:11]2[CH2:16][CH2:15][C:14]([N:18]3[CH2:22][CH2:21][CH:20]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=4[Cl:31])[C:19]3=[O:32])([CH3:17])[CH2:13][CH2:12]2)=O)=CC=1)([O-])=O.C([O-])([O-])=O.[K+].[K+]>CO>[Cl:31][C:25]1[CH:26]=[C:27]([Cl:30])[CH:28]=[CH:29][C:24]=1[CH2:23][CH:20]1[CH2:21][CH2:22][N:18]([C:14]2([CH3:17])[CH2:15][CH2:16][CH:11]([OH:10])[CH2:12][CH2:13]2)[C:19]1=[O:32]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 59299481HCID 59299481, compound

Product 1

HCID 59299359HCID 59299359, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 4-(3-(2,4-dichlorobenzyl)-2-oxopyrrolidin-1-yl)-4-methylcyclohexyl 4-nitrobenzoate (Preparation 57) (0.38 g, 0.76 mmol) in MeOH (50 mL). Add K2CO3 (0.21 g, 1.52 mmol) and stir the reaction overnight at room temperature. Add water (50 mL) and extract the aqueous with EtOAc (3×100 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 50-80% of EtOAc/Hexane) to give 0.24 g (91%) of the title compound as a white solid. MS (APCI-pos mode) m/z (rel intensity) 356.0 (100), 358.0 (60).

Workup

  1. customthe reaction overnight at room temperature
  2. extractionAdd water (50 mL) and extract the aqueous with EtOAc (3×100 mL)
  3. dry with materialCombine the organic layers and dry with Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate
  6. custompurify by flash column chromatography (silica gel, 50-80% of EtOAc/Hexane)

Sources & evidence

ORD record
ord-2450bfdc96aa42d1bacba63ee13eb0f0
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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