Sodium Hydroxide → 2(S)-Ethoxy-3-[4-(2-methylaminothiazol-5-yl)phenyl]propanoic acid

HRID 1864547Notes

Reaction equation

HRID 1864547 reaction equation
C([CH2:4][NH:5][C:6]1[S:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C@H:18]([O:23][CH2:24][CH3:25])[C:19]([O:21]C)=[O:20])=[CH:13][CH:12]=2)=[CH:9][N:10]=1)(=O)C.[OH-].[Na+]>CO.O>[CH2:24]([O:23][C@@H:18]([CH2:17][C:14]1[CH:13]=[CH:12][C:11]([C:8]2[S:7][C:6]([NH:5][CH3:4])=[N:10][CH:9]=2)=[CH:16][CH:15]=1)[C:19]([OH:21])=[O:20])[CH3:25]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86606237methyl 3-{4-[2-(acetylmethylamino)thiazol-5-yl]phenyl}-2(S)-ethoxypropanoate

Product 1

HCID 866062382(S)-Ethoxy-3-[4-(2-methylaminothiazol-5-yl)phenyl]propanoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

0.6 g (1.6 mmol) of methyl 3-{4-[2-(acetylmethylamino)thiazol-5-yl]phenyl}-2(S)-ethoxypropanoate in 25 ml of methanol and 2.4 ml (2.4 mmol) of aqueous 1M sodium hydroxide solution are heated at 60° C. for 18 hours. The reaction medium is cooled, diluted with water, acidified to pH 4-5 and then extracted with ethyl acetate and n-butanol. The organic phase is washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered and evaporated. The residue obtained is used in step h without purification.

Workup

  1. temperatureThe reaction medium is cooled
  2. extractionextracted with ethyl acetate and n-butanol
  3. washThe organic phase is washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue obtained
  8. customis used in step h without purification

Sources & evidence

ORD record
ord-904a8860ac304ca2a65f0cdab5cd1557
Source dataset
uspto-grants-2009_12
Patent number
US07625914B2

Reaction notes

Loading…