Ethanol → HCID 44251688, compound

HRID 1257446Notes

Reaction equation

HRID 1257446 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]([CH2:14][C:15]3[CH:24]=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[CH:17][CH:16]=3)[S:12][CH:13]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(O)C.[OH-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]([CH2:14][C:15]3[CH:24]=[CH:23][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=3)[S:12][CH:13]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 58127683HCID 58127683, compound

Product 1

HCID 44251688HCID 44251688, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the compound (352 mg, 0.931 mmol) obtained in Example 179a were added ethanol (4 mL), tetrahydrofuran (1 mL) and 2N aqueous sodium hydroxide solution (0.93 mL, 1.86 mmol), and the mixture was stirred overnight. The reaction mixture was extracted with water, and washed with ether. The aqueous layer was acidified with 6N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give the title compound (261 mg, 77%) as colorless crystals.

Workup

  1. extractionThe reaction mixture was extracted with water
  2. washwashed with ether
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-bd07beb9f8814f3591db13c6415fdaa3
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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