Lithium hydroxide, monohydrate → HCID 67190046, compound

HRID 546169Notes

Reaction equation

HRID 546169 reaction equation
C[O:2][C:3](=[O:21])[CH:4]([C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[C:12]([Cl:20])[CH:11]=1)[CH2:5][CH:6]1[CH2:9][O:8][CH2:7]1.O.[OH-].[Li+]>CO.O>[Cl:20][C:12]1[CH:11]=[C:10]([CH:4]([CH2:5][CH:6]2[CH2:9][O:8][CH2:7]2)[C:3]([OH:21])=[O:2])[CH:15]=[CH:14][C:13]=1[S:16]([CH3:19])(=[O:17])=[O:18]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67190044HCID 67190044, compound

Product 1

HCID 67190046HCID 67190046, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

2-(3-Chloro-4-methanesulfonyl-phenyl)-3-oxetan-3-yl-propionic acid methyl ester (1.0 g, 3.00 mmol) was dissolved in methanol (50 ml) and treated with a solution of lithium hydroxide monohydrate (0.50 g, 11.92 mmol) in water (1 ml) at 25° C. It was stirred at 25° C. for 1.5 h. The reaction was then concentrated in vacuo to remove the methanol. The remaining aqueous layer was then diluted with water and acidified to pH=3 with an aqueous 1N hydrochloric acid solution. This was then extracted with methylene chloride (3×50 mL), the organic layers combined and dried over magnesium sulfate, filtered and concentrated in vacuo to afford 2-(3-chloro-4-methanesulfonyl-phenyl)-3-oxetan-3-yl-propionic acid (0.87 g, 91%) as a white solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 2.01-2.14 (m, 1H, CH of CH2), 2.25-2.41 (m, 1H, CH of CH2), 2.75-2.89 (m, 1H, CH), 3.36 (s, 3H, SO2CH3), 3.68 (t, J=7.8 Hz, 1H, ArCHCO), 4.13 (t, J=6.3 Hz, 1H, OCH of OCH2), 4.27 (t, J=6.3 Hz, 1H, OCH of OCH2), 4.44 (dd, J=7.9, 5.9 Hz, 1H, OCH of OCH2), 4.57 (dd, J=7.9, 5.9 Hz, 1H, OCH of OCH2), 7.54 (dd, Jo=8.1 Hz, Jm=1.7 Hz, 1H, Ar), 7.68 (d, Jm=1.7 Hz, 1H, Ar), 8.00 (d, Jo=8.1 Hz, 1H, Ar), 12.77 (brs, 1H, CO2H).

Workup

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

Sources & evidence

ORD record
ord-ac7182ba823a4df490849fc96dac3924
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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