Hydrochloric Acid → HCID 59331360, compound

HRID 1881953Notes

Reaction equation

HRID 1881953 reaction equation
[CH:1]1([CH2:6][CH:7]([C:18]2[NH:22][C:21]([C:23]([O:25]CC)=[O:24])=[C:20]([CH3:28])[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.O.[OH-].[Li+].Cl>O1CCCC1>[CH:1]1([CH2:6][CH:7]([C:18]2[NH:22][C:21]([C:23]([OH:25])=[O:24])=[C:20]([CH3:28])[CH:19]=2)[C:8]2[CH:9]=[CH:10][C:11]([S:14]([CH3:17])(=[O:15])=[O:16])=[CH:12][CH:13]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 59331259HCID 59331259, compound

Product 1

HCID 59331360HCID 59331360, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution (10 mL) of ethyl 5-{2-cyclopentyl-1-[4-(methylsulfonyl)phenyl]ethyl}-3-methyl-1H-pyrrole-2-carboxylate (200 mg) in tetrahydrofuran was added an aqueous solution (2 mL) of lithium hydroxide monohydrate (65 mg), and the mixture was stirred at 50° C. overnight. The reaction mixture was slowly warmed to room temperature and stirred overnight. After cooling to room temperature, the reaction mixture was neutralized with 1N hydrochloric acid. The ethyl acetate layer was washed with water and saturated brine, dried (MgSO4) and concentrated to give the title compound (165 mg, yield 89%) as white crystals. melting point 127° C.

Workup

  1. temperatureThe reaction mixture was slowly warmed to room temperature
  2. stirringstirred overnight
  3. temperatureAfter cooling to room temperature
  4. washThe ethyl acetate layer was washed with water and saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f42658c1d7f9487e88ba81605e6b084e
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

Loading…