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

HRID 910295Notes

Reaction equation

HRID 910295 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-7e0ac5f24cf64213aded61f6031b6b17
Source dataset
uspto-grants-2011_09
Patent number
US08022079B2

Reaction notes

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