Potassium Hydroxide → HCID 21958970, compound

HRID 2214036Notes

Reaction equation

HRID 2214036 reaction equation
C[O:2][C:3](=[O:22])[CH:4]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1)[CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][O:7]1.[OH-].[K+]>C(O)C.O>[CH3:21][S:18]([C:15]1[CH:16]=[CH:17][C:12]([CH:4]([CH2:5][CH:6]2[CH2:11][CH2:10][CH2:9][CH2:8][O:7]2)[C:3]([OH:22])=[O:2])=[CH:13][CH:14]=1)(=[O:20])=[O:19]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67482160HCID 67482160, compound

Product 1

HCID 21958970HCID 21958970, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-(4-methanesulfonyl-phenyl)-3-(tetrahydro-pyran-2-yl)-propionic acid methyl ester (prepared as in Example 8, 75 mg, 0.23 mmol) in ethanol (5 mL) was treated with a solution of potassium hydroxide (32 mg, 0.58 mmol) in water (1 mL). The reaction was stirred for 3 h at 25° C. The reaction was then concentrated in vacuo to remove the ethanol and then acidified to pH=2 with a 1N aqueous hydrochloric acid solution. This solution was then extracted with methylene chloride (3×15 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, hexanes to 60/40 hexanes/ethyl acetate plus 1% acetic acid) afforded 2-(4-methanesulfonyl-phenyl)-3-(tetrahydro-pyran-2-yl)-propionic acid (60 mg, 85%) as a white solid: FAB-HRMS m/e calcd for C15H20O5S (M+H)+ 313.1109, found 313.1111.

Workup

  1. concentrationThe reaction was then concentrated in vacuo
  2. customto remove the ethanol
  3. extractionThis solution was then extracted with methylene chloride (3×15 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5b95f5d26a5d4196a2caa581da15f285
Source dataset
uspto-grants-2006_09
Patent number
US07105671B2

Reaction notes

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