Potassium Carbonate → HCID 178515595, compound

HRID 2235271Notes

Reaction equation

HRID 2235271 reaction equation
[Cl:1][C:2]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([C@@H:10]2[CH2:15][CH2:14][C@H:13]([O:16]C(=O)C3C=CC([N+]([O-])=O)=CC=3)[CH2:12][CH2:11]2)[C:6]1=[O:28].C([O-])([O-])=O.[K+].[K+]>CO>[Cl:1][C:2]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([C@H:10]2[CH2:11][CH2:12][C@@H:13]([OH:16])[CH2:14][CH2:15]2)[C:6]1=[O:28]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 178525742HCID 178525742, compound

Product 1

HCID 178515595HCID 178515595, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve cis-4-nitro-benzoic acid 4-[3-(2,4-dichloro-benzyl)-2-oxo-pyrrolidin-1-yl]-cyclohexyl ester (Example 16) (3.58 g, 7.29 mmol) in MeOH (200 mL). Add 2M K2CO3 (50 nL) and stir the reaction mixture overnight. Add water (200 mL) and extract the aqueous layer with ethyl acetate (3×300 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 50-100% of EtOAc-Hexane) to give 1.54 g (62%) of the title compound as a white solid. Mass spectrum (ion spray): m/z=342.0, 344.0 (M+1).

Workup

  1. extractionAdd water (200 mL) and extract the aqueous layer with ethyl acetate (3×300 mL)
  2. dry with materialCombine the organic layers and dry with Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate
  5. custompurify by flash column chromatography (silica gel, 50-100% of EtOAc-Hexane)

Sources & evidence

ORD record
ord-e3db3a4aa868440c972b16bdcd52f022
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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