Sulfuric Acid → (2S)-[3-Fluoro-4-(methylsulfonylamino)phenyl]propionic acid

HRID 238926Notes

Reaction equation

HRID 238926 reaction equation
C([C@H](N[C:12](=[O:27])[C@H:13]([C:15]1[CH:20]=[CH:19][C:18]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[C:17]([F:26])[CH:16]=1)[CH3:14])CO)C1C=CC=CC=1.[OH:28]S(O)(=O)=O>O1CCOCC1.O>[F:26][C:17]1[CH:16]=[C:15]([C@H:13]([CH3:14])[C:12]([OH:27])=[O:28])[CH:20]=[CH:19][C:18]=1[NH:21][S:22]([CH3:25])(=[O:23])=[O:24]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 24754390N-[(1S)-1-Benzyl-2-hydroxyethyl]-(2S)-2-[3-fluoro-4-(methylsulfonylamino)phenyl]propionamide

Product 1

HCID 24755464(2S)-[3-Fluoro-4-(methylsulfonylamino)phenyl]propionic acidYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of N-[(1S)-1-Benzyl-2-hydroxyethyl]-(2S)-2-[3-fluoro-4-(methylsulfonylamino)phenyl]propionamide (100 mg, 0.234 mmol) in 3 N H2SO4 (1 mL) and 1,4-dioxane (1 mL) was heated to 100° C. for 5 h and cooled to room temperature. The solution was diluted with water and extracted with CH2Cl2 several times. The combined organic layers were washed with water, dried over MgSO4, and concentrated in vacuo to afford (2S)-[3-Fluoro-4-(methylsulfonylamino)phenyl]propionic acid.

Workup

  1. extractionextracted with CH2Cl2 several times
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-60b3cfbb1be64939a1b4975b4652b13f
Source dataset
uspto-grants-2014_02
Patent number
US08642657B2

Reaction notes

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