Sodium Hydroxide → HCID 53246859, compound

HRID 1189590Notes

Reaction equation

HRID 1189590 reaction equation
[CH3:1][C:2]1[N:3]([CH2:29][C:30]([O:32]CC)=[O:31])[C:4]([CH3:28])=[C:5]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[S:20]([N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)(=[O:22])=[O:21])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[Na+]>O1CCCC1.O>[CH3:1][C:2]1[N:3]([CH2:29][C:30]([OH:32])=[O:31])[C:4]([CH3:28])=[C:5]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[S:20]([N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)(=[O:21])=[O:22])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67238453HCID 67238453, compound

Product 1

HCID 53246859HCID 53246859, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of ethyl 2-(2,5-dimethyl-3-phenyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (0.029 g, 0.060 mmol) in tetrahydrofuran (1 ml) and water (1 ml) was added 1N sodium hydroxide (0.121 ml, 0.121 mmol). Upon addition, the reaction changed color from pink to yellow. The mixture was stirred overnight, after which LCMS analysis indicated reaction completion. The reaction was quenched with 0.050 ml of 3N HCl and stirred to afford a pink color. The crude mixture was concentrated and taken up in acetonitrile and purified by reverse phase HPLC chromatography. Acetonitrile and water spiked with 0.1% TFA were used as eluents. The desired fractions were collected and quenched with aqueous saturated sodium bicarbonate solution and washed with ether. The aqueous layer was then acidified with 3N HCl to pH=1 and this aqueous layer was extracted 3 times with ether. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated to afford a purple solid (0.0203 g, 0.045 mmol, 74.3% yield). 1H NMR (CDCl3/400 MHz)ppm) 7.91 (d, 1H), 7.37-7.33 (m, 1H), 7.23-7.17 (m, 1H), 7.15-7.11 (m, 3H), 7.08-7.05 (m, 1H), 6.99-6.97 (m, 2H), 4.63 (s, 2H), 4.07 (s, 2H), 3.08-3.04 (m, 4H), 2.14 (s, 3H), 1.98 (s, 3H), 1.61-1.58 (m, 4H). LCMS (M+1): 453.3.

Workup

  1. additionUpon addition
  2. customreaction completion
  3. customThe reaction was quenched with 0.050 ml of 3N HCl
  4. stirringstirred
  5. customto afford a pink color
  6. concentrationThe crude mixture was concentrated
  7. custompurified by reverse phase HPLC chromatography
  8. customThe desired fractions were collected
  9. customquenched with aqueous saturated sodium bicarbonate solution
  10. washwashed with ether
  11. extractionthis aqueous layer was extracted 3 times with ether
  12. washThe combined organic layers were washed with brine
  13. dry with materialdried over sodium sulfate
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-8194861cd7b0412692960672aee3fd09
Source dataset
uspto-grants-2014_03
Patent number
US08674115B2

Reaction notes

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