Sodium Carbonate → HCID 69743182, compound

HRID 1760364Notes

Reaction equation

HRID 1760364 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:10][CH2:9][CH2:8][N:7]1[C:11]1[CH:12]=[N:13][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21](C=O)=[CH:20][CH:19]=2)=[CH:15][CH:16]=1)=[O:5])[CH3:2].[C:31](=[O:34])([O-:33])[O-].[Na+].[Na+].[Mn]([O-])(=O)(=O)=[O:38].[K+]>C(O)(C)(C)C.O>[CH2:29]([O:28][C:26]([C:6]1([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:10][CH2:9][C:8](=[O:38])[N:7]1[C:11]1[CH:12]=[N:13][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([C:31]([OH:33])=[O:34])=[CH:20][CH:19]=2)=[CH:15][CH:16]=1)=[O:27])[CH3:30]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 516875Potassium PermanganateHCID 86588174HCID 86588174, compound

Product 1

HCID 69743182HCID 69743182, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 714019492-Methylpropan-2-ol--water (1/1)Solvent

Procedure

A mixture of 1-[6-(4-Formyl-phenoxy)-pyridin-3-yl]-pyrrolidine-2,2-dicarboxylic acid diethyl ester (0.70 g, 1.64 mmol), sodium carbonate (0.26 g, 1.64 mmol) and 16.4 mL of 1:1 tert-butyl alcohol-water was treated with potassium permanganate (0.26 g, 1.64 mmol). After stirring for 2 hours at room temperature, the mixture was quenched with sodium sulfite, acidified with 1M hydrochloric acid and extracted 3× with ethyl acetate. The combined organic layers were dried over sodium sulphate, filtered and concentrated in vacuo, affording 1-[6-(4-Carboxy-phenoxy)-pyridin-3-yl]-5-oxo-pyrrolidine-2,2-dicarboxylic acid diethyl ester as a colorless syrup (0.5 g). 1H NMR (CDCl3, 500 MHz): 8.14 (d, 2H, J=8.5 Hz), 8.10 (d, 1H, J=3.0 Hz), 7.80 (dd, 1H, J=2.5, 8.5 Hz), 7.24 (d, 2H, J=8.0 Hz), 7.02 (d, 1H, J=9.0 Hz), 4.21 (q, 4H, J=7.0 Hz), 2.74 (m, 2H), 2.66 (m, 2H), 1.21 (t, 6H, J=7.5 Hz) ppm. MS (APCl, m/z): 443 [M+H]+.

Workup

  1. customthe mixture was quenched with sodium sulfite
  2. extractionextracted 3× with ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4980afd66cf64d40a3bc64c9d00b21fc
Source dataset
uspto-grants-2005_01
Patent number
US06841671B2

Reaction notes

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