Sodium Hydroxide → 2-(((Tert-butoxycarbonyl)amino)methyl)thiazole-4-carboxylic acid

HRID 1603463Notes

Reaction equation

HRID 1603463 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([NH:10][CH2:11][C:12]1[S:13][CH:14]=[C:15]([C:17]([O:19]CC)=[O:18])[N:16]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>C(O)C>[C:3]([O:7][C:8]([NH:10][CH2:11][C:12]1[S:13][CH:14]=[C:15]([C:17]([OH:19])=[O:18])[N:16]=1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9925901Ethyl 2-(((tert-butoxycarbonyl)amino)methyl)thiazole-4-carboxylate

Product 1

HCID 101990462-(((Tert-butoxycarbonyl)amino)methyl)thiazole-4-carboxylic acidYield 81.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 20 ml portion of a 2N aqueous sodium hydroxide solution was added to 100 ml of an ethanol solution containing 5.727 g of ethyl 2-(N-t-butoxycarbonylamino)methylthiazol-4-carboxylate, and the mixture was then stirred at room temperature for 45 minutes. After adjustment to pH 5 with 2N hydrochloric acid, the solvent was evaporated under reduced pressure. Further, the solution was dissolved in 300 ml of ethanol under heating, and after the removal of a salt by filtration, the solvent was evaporated under reduced pressure to obtain 4.228 g of 2-(N-t-butoxycarbonylamino)methylthiazol-4-carboxylic acid as a milky white solid.

Workup

  1. customAfter adjustment to pH 5 with 2N hydrochloric acid, the solvent was evaporated under reduced pressure
  2. dissolutionFurther, the solution was dissolved in 300 ml of ethanol
  3. temperatureunder heating
  4. customafter the removal of a salt
  5. filtrationby filtration
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b8d5235534974f40b26ce946130aa33e
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

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