Hydrochloric Acid → 2-[3-Fluoro-4-(metylsulfonylamino)phenyl]propion

HRID 238923Notes

Reaction equation

HRID 238923 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:13]([CH3:19])[C:14]([O:16]CC)=O)[CH:5]=[CH:6][C:7]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10].[OH-].[Li+].Cl.[CH2:23]1COC[CH2:24]1>O.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:13]([C:14]([CH2:23][CH3:24])=[O:16])[CH3:19])[CH:5]=[CH:6][C:7]=1[NH:8][S:9]([CH3:12])(=[O:10])=[O:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 24754385Ethyl 2-[3-fluoro-4-(metylsulfonylamino)phenyl]propionate

Product 1

HCID 1317311832-[3-Fluoro-4-(metylsulfonylamino)phenyl]propionYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 2-[3-fluoro-4-(metylsulfonylamino)phenyl]propionate (1-26, 2 mmol) in H2O and THF (1:2, 30 mL) was treated with lithium hydroxide (6 mmol) and stirred for 4 h at room temperature. The mixture was diluted with H2O and CH2Cl2, acidified by 1 N HCl solution and extracted with CH2Cl2 several times. The combined organic layers were washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was crystallized by diethyl ether and n-hexane to afford 2-[3-fluoro-4-(metylsulfonylamino)phenyl]propion acid compound (1-38, SU-660)

Workup

  1. extractionextracted with CH2Cl2 several times
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was crystallized by diethyl ether and n-hexane

Sources & evidence

ORD record
ord-2ce7cc853b264ab991f4e8b804a00717
Source dataset
uspto-grants-2014_02
Patent number
US08642657B2

Reaction notes

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