Lithium Hydroxide → 2-(3-Cyano-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid

HRID 398547Notes

Reaction equation

HRID 398547 reaction equation
C[O:2][C:3](=[O:23])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[C:13]([C:21]#[N:22])[CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Li+]>O1CCCC1>[C: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:23])=[O:2])[CH:16]=[CH:15][C:14]=1[S:17]([CH3:20])(=[O:18])=[O:19])#[N:22]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 12069498HCID 12069498, compound

Product 1

HCID 120694992-(3-Cyano-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acidYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-(3-cyano-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid methyl ester (4.84 g, 14.4 mol) in tetrahydrofuran (25 mL) was treated with a 0.8M aqueous lithium hydroxide solution (27 mL, 21.6 mmol). The reaction mixture was stirred at 25° C. for 2.5 h. The reaction mixture was partitioned between water and ethyl acetate and then acidified to pH=2 with a 10% aqueous hydrochloric acid solution. The layers were shaken and separated. The resulting organic layer was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford crude 2-(3-cyano-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid (3.80 g, 82%) as a pale yellow oil that solidified to a pale yellow solid. An analytical sample was obtained by recrystallization from ethyl acetate to afford 2-(3-cyano-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid as a white solid: mp 180-181° C.; EI-HRMS m/e calcd for C16H19NO4S (M+) 321.1034, found 321.1039.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. stirringThe layers were shaken
  3. customseparated
  4. washThe resulting organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1542a24160264339a9a70b9444c70f23
Source dataset
uspto-grants-2003_08
Patent number
US06610846B1

Reaction notes

Loading…