Lithium hydroxide, monohydrate → HCID 67191193, compound

HRID 546150Notes

Reaction equation

HRID 546150 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][C@H:6]1[CH2:10][CH2:9][CH2:8][O:7]1.O.[OH-].[Li+]>C(O)C.O>[Cl:21][C:13]1[CH:12]=[C:11]([CH:4]([CH2:5][C@H:6]2[CH2:10][CH2:9][CH2:8][O: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 67190125HCID 67190125, compound

Product 1

HCID 67191193HCID 67191193, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

2-(3-chloro-4-methanesulfonyl-phenyl)-3-(tetrahydro-furan-2(R)-yl)-propionic acid methyl ester (180 mg, 0.52 mmol) was dissolved in ethanol (5 mL) and treated with a solution of lithium hydroxide monohydrate (54 mg, 1.3 mmol) in water (1 mL) at 25° C. It was stirred at 25° C. until the starting material was all consumed by TLC. The reaction was then concentrated in vacuo to remove the ethanol. The remaining aqueous layer was then acidified to pH=2 with an aqueous 1N hydrochloric acid solution. This was then extracted with ethyl acetate (3×20 mL), the organic layers combined and dried over magnesium sulfate, filtered and concentrated in vacuo to afford 2-(3-chloro-4-methanesulfonyl-phenyl)-3-(tetrahydro-furan-2(R)-yl)-propionic acid (168 mg, 98%) as a reaction of two diastereomers as a white foam: ES-HRMS m/e calcd for C14H17O5SCl (M+H)+ 333.0558, observed 333.0553; 1H NMR (300 MHz, DMSO-d6) δ ppm 1.35-1.49 (m, 1H, CH of CH2), 1.66-1.99 (m, 4H, 4×CH of CH2), 2.06-2.23 (m, 1H, CH of CH2), 3.34, 3.35 (2×s, 3H, SO2CH3), 3.42-3.85 (m, 4H, OCH2 and OCH and ArCH), 7.54 (2×dd, Jo=8.1 Hz, Jm=1.7 Hz, 1H, Ar), 7.66 (2×d, Jm=1.7 Hz, 1H, Ar), 7.99 (2×d, Jo=8.1 Hz, 1H, Ar), 12.69 (brs, 1H, CO2H).

Workup

  1. customall consumed by TLC
  2. concentrationThe reaction was then concentrated in vacuo
  3. customto remove the ethanol
  4. extractionThis was then extracted with ethyl acetate (3×20 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-48e051f5313c41c0a95763ba2701549b
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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