Potassium Hydroxide → HCID 59576357, compound

HRID 2069516Notes

Reaction equation

HRID 2069516 reaction equation
C[O:2][C:3]([C:5]1[N:6]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=2)[CH:7]=[C:8]([S:10]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)(=[O:12])=[O:11])[CH:9]=1)=[O:4].[OH-].[K+]>C(O)C.O>[F:26][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][C:22]=1[F:25])[CH2:18][N:6]1[CH:7]=[C:8]([S:10]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)(=[O:12])=[O:11])[CH:9]=[C:5]1[C:3]([OH:4])=[O:2]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 59576362HCID 59576362, compound

Product 1

HCID 59576357HCID 59576357, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-(3,4-difluoro-benzyl)-4-(thiophene-2-sulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester (D1-II) in ethanol was added potassium hydroxide in water and stirred overnight at room temperature. Solvent was removed under reduced pressure; the residue was taken in water and washed with diethyl ether. The aqueous layer was acidified with dilute HCl and precipitate was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulphate, filtered and concentrated to afford 1-(3,4-difluoro-benzyl)-4-(thiophene-2-sulfonyl)-1H-pyrrole-2-carboxylic acid (D1-III).

Workup

  1. customSolvent was removed under reduced pressure
  2. washwashed with diethyl ether
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7ce4cf7b35814ca0822730c975c012eb
Source dataset
uspto-grants-2012_10
Patent number
US08299115B2

Reaction notes

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