Potassium Hydroxide → 1-(phenylsulfonyl)-1H-pyrrole-2-carboxylic acid

HRID 59726Notes

Reaction equation

HRID 59726 reaction equation
[C:1]1([S:7]([N:10]2[CH:14]=[CH:13][CH:12]=[C:11]2[C:15]([O:17]C)=[O:16])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+]>CO.C1COCC1>[C:1]1([S:7]([N:10]2[CH:14]=[CH:13][CH:12]=[C:11]2[C:15]([OH:17])=[O:16])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 10879987HCID 10879987, compound2×

Product 1

HCID 836539291-(phenylsulfonyl)-1H-pyrrole-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 1-(phenylsulfonyl)-1H-pyrrole-2-carboxylate (Intermediate 1) (500 mg, 1.885 mmol) in MeOH (7 ml) and THF (7 ml) cooled to 0° C., aqueous 1N KOH (2.827 ml, 2.83 mmol) was added drop-wise and the resulting mixture was stirred at RT for 24 hours. UPLC-MS analysis showed the presence of desired compound in admixture with methyl 1H-pyrrole-2-carboxylate as the main product. The mixture was poured into ice-water and washed with DCM. The aqueous phase was acidified with 37% HCl (pH=2) and extracted with DCM. The organic layer was dried over sodium sulfate, filtered and evaporated to afford a mixture of 1-(phenylsulfonyl)-1H-pyrrole-2-carboxylic acid (Intermediate 2) (MS/ESI+252.0 [MH]+) and methyl 1H-pyrrole-2-carboxylate (MS/ESI+126.0 [MH]+) (234 mg, ratio about 3/7). This mixture was used as such in the next step.

Sources & evidence

ORD record
ord-0badda59c1d649039bffd2214b5b4303
Source dataset
uspto-grants-2016_09
Patent number
US09440954B2

Reaction notes

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