Lithium hydroxide, monohydrate → 2-(3-Chloro-4-methanesulfonyl-phenyl)-3-(tetrahydro-furan-3-yl)-propionic acid

HRID 546159Notes

Reaction equation

HRID 546159 reaction equation
C[O:2][C:3](=[O:22])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[C:13]([Cl:21])[CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][O:8][CH2:7]1.O.[OH-].[Li+]>CO.O>[Cl:21][C:13]1[CH:12]=[C:11]([CH:4]([CH2:5][CH:6]2[CH2:10][CH2:9][O:8][CH2:7]2)[C:3]([OH:22])=[O:2])[CH:16]=[CH:15][C:14]=1[S:17]([CH3:20])(=[O:19])=[O:18]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67190185HCID 67190185, compound

Product 1

HCID 219590572-(3-Chloro-4-methanesulfonyl-phenyl)-3-(tetrahydro-furan-3-yl)-propionic acidYield 84%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

2-(3-Chloro-4-methanesulfonyl-phenyl)-3-(tetrahydro-furan-3-yl)-propionic acid methyl ester (0.85 g, 2.45 mmol) was dissolved in methanol (10 ml) and treated with a solution of lithium hydroxide monohydrate (0.51 g, 12.15 mmol) in water (1 ml) at 25° C. It was stirred at 25° C. for 2 h or until the starting material was all consumed by TLC. The reaction was then concentrated in vacuo to remove the methanol. The remaining aqueous layer was then diluted with water and acidified to pH=2 with an aqueous 1N hydrochloric acid solution. This was then extracted with methylene chloride (2×50 mL). The organic layers were combined and dried over magnesium sulfate, filtered and concentrated in vacuo to afford 2-(3-chloro-4-methanesulfonyl-phenyl)-3-(tetrahydro-furan-3-yl)-propionic acid (0.68 g, 84%) as a white solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.41-1.56 (m, 1H, CH of CH2), 1.74-2.12 (m, 4H, CH and 3×CH of 2×CH2), 3.16-3.30 (m, 1H, OCH of OCH2), 3.37 (s, 3H, SO2CH3), 3.51-3.79 (m, 4H, ArCH and 3×OCH of 2×OCH2), 7.57 (2×dd, Jo=8.3 Hz, Jm=1.7 Hz, 1H, Ar), 7.71 (2×d, Jm=1.7 Hz, 1H, Ar), 8.00 (2×d, Jo=8.3 Hz, 1H, Ar), 12.76 (brs, 1H, CO2H).

Workup

  1. customall consumed by TLC
  2. concentrationThe reaction was then concentrated in vacuo
  3. customto remove the methanol
  4. additionThe remaining aqueous layer was then diluted with water
  5. extractionThis was then extracted with methylene chloride (2×50 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9cdbf03a67ad4168a5a9018e0b0fc500
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

Loading…