Hydrochloric Acid → 5-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrole-2-carboxylic acid

HRID 909457Notes

Reaction equation

HRID 909457 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]([CH3:33])[O:5][C:6]1[CH:7]=[C:8]([C:23]2[NH:27][C:26]([C:28]([O:30]CC)=[O:29])=[CH:25][CH:24]=2)[CH:9]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)[CH:11]=1.[OH-].[Na+].Cl>C(O)C>[CH3:1][O:2][CH2:3][C@H:4]([CH3:33])[O:5][C:6]1[CH:7]=[C:8]([C:23]2[NH:27][C:26]([C:28]([OH:30])=[O:29])=[CH:25][CH:24]=2)[CH:9]=[C:10]([O:12][C:13]2[CH:14]=[CH:15][C:16]([S:19]([CH3:22])(=[O:20])=[O:21])=[CH:17][CH:18]=2)[CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58065515Ethyl 5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrole-2-carboxylate

Product 1

HCID 666818155-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrole-2-carboxylic acidYield 99.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrole-2-carboxylate (4.36 g, 9.2 mmol) synthesized in Example (17d) was dissolved in ethanol (100 mL), and a 4N aqueous sodium hydroxide solution (23 mL, 92 mmol) was added, followed by heating to reflux for 1 hour under nitrogen atmosphere. To the reaction solution, 2N hydrochloric acid (45 mL) was added to neutralize it, and the solvent was distilled off under reduced pressure. 1N hydrochloric acid was used to make the solution acidic, and extraction was carried out with ethyl acetate (300 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, to afford the desired product (4.06 g, yield 99%) as a white solid.

Workup

  1. temperatureby heating
  2. temperatureto reflux for 1 hour under nitrogen atmosphere
  3. distillationthe solvent was distilled off under reduced pressure
  4. extractionextraction
  5. washThe organic layer was washed with saturated brine
  6. dry with materialsubsequently dried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-05380eb0ce9f427fa0ce10c694bb8e4e
Source dataset
uspto-grants-2011_09
Patent number
US08017610B2

Reaction notes

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