Hydrochloric Acid → HCID 11610770, compound

HRID 1883472Notes

Reaction equation

HRID 1883472 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]([O:10][CH2:11][CH2:12][S:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)=[O:9])[CH:4]=[C:3]1[C:24]([O:26]C)=[O:25].[Li+].[OH-].Cl>C1COCC1.O>[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]([O:10][CH2:11][CH2:12][S:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:18][CH:19]=2)=[O:9])[CH:4]=[C:3]1[C:24]([OH:26])=[O:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 11188835HCID 11188835, compound

Product 1

HCID 11610770HCID 11610770, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Methyl 1-methyl-4-[2-(4-trifluoromethyl-phenylsulfanyl)-ethoxycarbonylamino]-1H-pyrrole-2-carboxylate (5.0 g, 12.43 mmol) prepared in the capping step was dissolved in THF/H2O (200 ml/100 ml), 1N LiOH (30 ml) was added thereto, and the mixture was stirred for 4 days at room temperature. The reaction solution was acidified to pH 2.0 by 1N HCl and then extracted with EA and water. The organic layer was washed with aqueous NaCl solution and dried over anhydrous MgSO4. The solvent contained therein was removed to give a white solid, which was then recrystallized from EA and n-hexane to give 1-methyl-4-[2-(4-trifluoromethyl-phenylsulfanyl)-ethoxy carbonylamino]-1H-pyrrole-2-carboxylic acid (3.20 g, 66.29%) of a pale yellow solid.

Workup

  1. extractionextracted with EA and water
  2. washThe organic layer was washed with aqueous NaCl solution
  3. dry with materialdried over anhydrous MgSO4
  4. customThe solvent contained therein was removed
  5. customto give a white solid, which
  6. customwas then recrystallized from EA and n-hexane

Sources & evidence

ORD record
ord-de65d8c947f24d2e88031a2a0b78f336
Source dataset
uspto-grants-2004_07
Patent number
US06759511B2

Reaction notes

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