Lithium Hydroxide → HCID 22315251, compound

HRID 430290Notes

Reaction equation

HRID 430290 reaction equation
C[O:2][C:3](=[O:25])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[C:13]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Li+]>O1CCCC1>[CH3:24][S:21]([C:13]1[CH:12]=[C:11]([CH:4]([CH2:5][CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)[C:3]([OH:25])=[O:2])[CH:16]=[CH:15][C:14]=1[S:17]([CH3:20])(=[O:19])=[O:18])(=[O:23])=[O:22]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 54445655HCID 54445655, compound

Product 1

HCID 22315251HCID 22315251, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-(3,4-bis-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid methyl ester (1.17 g, 3.01 mmol) in tetrahydrofuran (12 mL) was treated with a 0.8M aqueous lithium hydroxide solution (5.6 mL, 4.52 mmol). The reaction mixture was stirred at 25° C. for 3 h. The resulting reaction mixture was partitioned between water (75 mL) and ethyl acetate (75 mL) and then treated with a 1N aqueous hydrochloric acid solution (10 mL). The layers were shaken and separated. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 2-(3,4-bis-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid (1.10 g, 98%) as a white foam which was used without further purification: mp 64-68° C. (foam to gel); FAB-HRMS m/e calcd for C16H22O6S2 (M+H)+ 375.0936, found 375.0932.

Workup

  1. customThe resulting reaction mixture
  2. customwas partitioned between water (75 mL) and ethyl acetate (75 mL)
  3. additiontreated with a 1N aqueous hydrochloric acid solution (10 mL)
  4. stirringThe layers were shaken
  5. customseparated
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f7a11d49fdf2484397e033a141f9c500
Source dataset
uspto-grants-2001_11
Patent number
US06320050B1

Reaction notes

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