Hydrochloric Acid → HCID 53246498, compound

HRID 1189578Notes

Reaction equation

HRID 1189578 reaction equation
[C:1]([C:4]1[C:8]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:18])=[O:17])=[C:7]([CH3:25])[N:6]([CH2:26][C:27]([O:29]CC)=[O:28])[C:5]=1[CH3:32])(=[O:3])[CH3:2].[Li+].[OH-].CCOC(C)=O.Cl>CO.C1COCC1.O>[C:1]([C:4]1[C:8]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:17])=[O:18])=[C:7]([CH3:25])[N:6]([CH2:26][C:27]([OH:29])=[O:28])[C:5]=1[CH3:32])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 58310938HCID 58310938, compound

Product 1

HCID 53246498HCID 53246498, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To the crude mixture of ethyl 2-(3-acetyl-2,5-dimethyl-4-(2-(phenylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (25 mg, 0.055 mmol) in MeOH:THF:water 3:3:1 (5 ml total) was added LiOH (3.96 mg, 0.165 mmol) and the resulting mixture was stirred for 30 min. To this mixture were added EtOAc (3 mL) and HCl (1N aq., 3 mL). The ethyl acetate layer was separated and dried over Na2SO4, filtered and subjected to column chromatography on silica gel (0 to 100% ethyl acetate in hexanes, followed by 0 to 20% MeOH in ethyl acetate). Collection and concentration of pertinent fractions resulted in the isolation of 2-(3-acetyl-2,5-dimethyl-4-(2-(phenylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetic acid (10.5 mg, 45%) as a tan solid. 1H NMR (CDCl3/400 MHz) 8.23-8.20 (m, 1H), 7.84 (d, 2H), 7.51 (t, (t, 1H), 7.48-7.40 (m, 2H), 7.36-7.30 (m, 2H), 6.84-6.21 (m, 1H), 4.51 (s, 2H), 4.09 (s, 2H), 2.37 (s, 3H), 1.79 (s, 3H), 1.62 (s, 3H). MS m/z=426.4 (M+1).

Workup

  1. customThe ethyl acetate layer was separated
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customCollection and concentration of pertinent fractions

Sources & evidence

ORD record
ord-4b02e4811bc84b57add0cff682b535a5
Source dataset
uspto-grants-2014_03
Patent number
US08674115B2

Reaction notes

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