Hydrochloric Acid → 2-(2-methyl-4,5-diphenyl-3-(2-(phenylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetic acid

HRID 1189561Notes

Reaction equation

HRID 1189561 reaction equation
[CH3:1][C:2]1[N:3]([CH2:35][C:36]([O:38]CC)=[O:37])[C:4]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:5]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:6]=1[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15].[OH-].[Li+].Cl>C1COCC1.CO.O>[CH3:1][C:2]1[N:3]([CH2:35][C:36]([OH:38])=[O:37])[C:4]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[C:5]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:6]=1[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:15])=[O:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 53246024HCID 53246024, compound

Product 1

HCID 532460272-(2-methyl-4,5-diphenyl-3-(2-(phenylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetic acidYield 100%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Ethyl 2-(2-methyl-4,5-diphenyl-3-(2-(phenylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (0.300 g, 0.546 mmol) was dissolved in a 3:1:1 mixture of THF/MeOH/water (10 ml) and charged with lithium hydroxide (0.065 g, 2.73 mmol). The reaction was stirred at rt for 1 h, at which time LC/MS suggested the reaction was complete. The reaction was acidified with 3 N HCl, and the resulting mixture concentrated to almost dryness (water left), diluted with 3 mL brine solution and extracted 3 times with DCM. The organic layers were combined, dried, filtered, and concentrated under vacuum to yield 2-(2-methyl-4,5-diphenyl-3-(2-(phenylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetic acid (285 mg, 0.546 mmol, 100% yield).

Workup

  1. concentrationthe resulting mixture concentrated to almost dryness (water left)
  2. additiondiluted with 3 mL brine solution
  3. extractionextracted 3 times with DCM
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-333197ce4ddc4dd58e1d8b36a71d8f6b
Source dataset
uspto-grants-2014_03
Patent number
US08674115B2

Reaction notes

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