Sodium Hydroxide → HCID 19883554, compound

HRID 1947737Notes

Reaction equation

HRID 1947737 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]([CH3:12])[C:7]([O:9]CC)=[O:8].[OH-].[Na+]>CO>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]([CH3:12])[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21835134HCID 21835134, compound

Product 1

HCID 19883554HCID 19883554, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.26 g (1.5 mmol) of ethyl 2-(1,3-thiazol-2-yl)propanoate from step A above in 15 mL of methanol was added 3.0 mL (15 mmol) of an aqueous 5.0 M sodium hydroxide solution. The resulting mixture was stirred at ambient temperature overnight. The reaction mixture was evaporated in vacuo to remove the methanol and the aqueous phase was acidified with a 2 N hydrochloric acid solution until a pH of 4 was achieved. The aqueous solution was purified by reverse phase HPLC (TMC Pro-Pac C18; 0-25% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient). The pure fractions were lyophilized overnight to afford the title compound as a white solid (0.17 g, 71%). LC-MS: m/z (ES) 158 (MH)+.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customto remove the methanol
  3. customThe aqueous solution was purified by reverse phase HPLC (TMC Pro-Pac C18; 0-25% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient)
  4. waitThe pure fractions were lyophilized overnight

Sources & evidence

ORD record
ord-6eb148a8bf08450289ca3091390fd1e8
Source dataset
uspto-grants-2013_03
Patent number
US08399480B2

Reaction notes

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