Hydrochloric Acid → HCID 178524388, compound

HRID 423193Notes

Reaction equation

HRID 423193 reaction equation
[CH:1]1([CH:7]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([C:18]4[CH:22]=[CH:21][O:20][N:19]=4)=[CH:14][CH:13]=3)[C:10](=[O:23])[C:9]([OH:24])=[C:8]2[C:25](=[O:36])[C:26]2[CH:31]=[CH:30][C:29]([C:32]([O:34]C)=[O:33])=[CH:28][CH:27]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1COCC1.[OH-].[Na+].Cl>O.C(OCC)(=O)C.CO>[CH:1]1([CH:7]2[N:11]([C:12]3[CH:13]=[CH:14][C:15]([C:18]4[CH:22]=[CH:21][O:20][N:19]=4)=[CH:16][CH:17]=3)[C:10](=[O:23])[C:9]([OH:24])=[C:8]2[C:25](=[O:36])[C:26]2[CH:31]=[CH:30][C:29]([C:32]([OH:34])=[O:33])=[CH:28][CH:27]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 178497960HCID 178497960, compound

Product 1

HCID 178524388HCID 178524388, compoundYield 88.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 5-cyclohexyl-3-hydroxy-1-(4-isoxazol-3-ylphenyl)-4-(4-methoxycarbonylbenzoyl)-1,5-dihydropyrrol-2-one (1.98 g, 4.07 mmol), THF (20 mL) and methanol (13 mL) was added aqueous 2N sodium hydroxide (5.09 mL). The mixture was stirred at 80° C. for 2 hr. To the mixture was added 2N hydrochloric acid (5.09 mL) under ice-cooling conditions, and ethyl acetate and water were added. The mixture was stirred at r.t. overnight. The precipitate was collected by filtration to give 5-cyclo hexyl-3-hydroxy-1-(4-isoxazol-3-ylphenyl)-4-(4-carboxybenzoyl)-1,5-dihydropyrrol-2-one (1.70 g, 88%) as yellow crystals.

Workup

  1. additionwere added
  2. stirringThe mixture was stirred at r.t. overnight
  3. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-4630b615cc394586ab1a74820512f56a
Source dataset
uspto-grants-2012_01
Patent number
US08101644B2

Reaction notes

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