Hydrochloric Acid → 4-[4-(2,4-Dioxobicyclo[3.2.1]oct-3-yl)-5-methylthiophen-2-yl]benzoic acid

HRID 45906Notes

Reaction equation

HRID 45906 reaction equation
C[O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][C:12]([CH3:25])=[C:13]([CH:15]3[C:21](=[O:22])[CH:20]4[CH2:23][CH:17]([CH2:18][CH2:19]4)[C:16]3=[O:24])[CH:14]=2)=[CH:6][CH:5]=1.[OH-].[Li+].Cl>CO>[O:24]=[C:16]1[CH:15]([C:13]2[CH:14]=[C:10]([C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:26])=[O:2])=[CH:5][CH:6]=3)[S:11][C:12]=2[CH3:25])[C:21](=[O:22])[CH:20]2[CH2:23][CH:17]1[CH2:18][CH2:19]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66741900HCID 66741900, compound

Product 1

HCID 667420604-[4-(2,4-Dioxobicyclo[3.2.1]oct-3-yl)-5-methylthiophen-2-yl]benzoic acidYield 77.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-[4-(2,4-dioxobicyclo[3.2.1]oct-3-yl)-5-methylthiophen-2-yl]benzoic acid methyl ester (60 mg, 0.16 mmol) in methanol (2 ml) is added 1N aqueous lithium hydroxide solution (2 ml) and the reaction stirred at room temperature for 72 hours. The reaction is acidified with 2N aqueous hydrochloric acid (25 ml) and extracted with dichloromethane (25 ml). The organic layer is washed with brine, dried over magnesium sulphate, filtered and the filtrate is concentrated in vacuo to give 4-[4-(2,4-dioxobicyclo[3.2.1]oct-3-yl)-5-methylthiophen-2-yl]benzoic acid (44 mg).

Workup

  1. extractionextracted with dichloromethane (25 ml)
  2. washThe organic layer is washed with brine
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-10657fb6d38f472da1fe1b05d6729656
Source dataset
uspto-grants-2013_09
Patent number
US08541594B2

Reaction notes

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