Water → 3-(naphthalene-2-sulfonamido)-3-phenylpropionic Acid

HRID 45986Notes

Reaction equation

HRID 45986 reaction equation
[Li+].[OH-].O.[CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]=1[S:14]([NH:17][CH:18]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:19][C:20]([O:22]C)=[O:21])(=[O:16])=[O:15]>CO.O>[CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]=1[S:14]([NH:17][CH:18]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:19][C:20]([OH:22])=[O:21])(=[O:15])=[O:16]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 57436805Methyl 3-(naphthalene-2-sulfonamido)-3-phenylpropionate

Product 1

HCID 36326413-(naphthalene-2-sulfonamido)-3-phenylpropionic Acid

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

LiOH×H2O (0.25 g, 18 mmol) was added to a solution of the methyl 3-(naphthalene-2-sulfonamido)-3-phenylpropionate (3.3 g, 9 mmol) in a methanol/water mixture (3:1, 90 ml) at a reaction temperature of 0° C. The reaction mixture was stirred at RT for 16 h. The solvent was removed under reduced pressure, the residue was taken up in water and the mixture was washed with MC. The aqueous phase was then cautiously acidified with HCl (1 N) and extracted with ethyl acetate. The organic phase was washed with water and sat. NaCl solution and dried over Na2SO4. After removal of the solvent, the product was obtained in an adequate purity.

Workup

  1. customThe solvent was removed under reduced pressure
  2. washthe mixture was washed with MC
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water and sat. NaCl solution
  5. dry with materialdried over Na2SO4
  6. customAfter removal of the solvent
  7. customthe product was obtained in an adequate purity

Sources & evidence

ORD record
ord-e857fceb68bb4a5a89abff8c18577fd7
Source dataset
uspto-grants-2013_09
Patent number
US08541573B2

Reaction notes

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