Sodium Hydroxide → 2-[2-(N-methyl-N-tert-pentyloxycarbonylamino)-1,3-thiazol-4-yl]glyoxylic acid

HRID 325378Notes

Reaction equation

HRID 325378 reaction equation
[CH3:1][N:2]([C:11]1[S:12][CH:13]=[C:14]([C:16](=[O:22])[C:17]([O:19]CC)=[O:18])[N:15]=1)[C:3]([O:5][C:6]([CH2:9][CH3:10])([CH3:8])[CH3:7])=[O:4].[OH-].[Na+]>C(O)C>[CH3:1][N:2]([C:11]1[S:12][CH:13]=[C:14]([C:16](=[O:22])[C:17]([OH:19])=[O:18])[N:15]=1)[C:3]([O:5][C:6]([CH2:9][CH3:10])([CH3:7])[CH3:8])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20254366ethyl 2-[2-(N-methyl-N-tert-pentyloxycarbonylamino)-1,3-thiazol-4-yl]glyoxylate

Product 1

HCID 202543752-[2-(N-methyl-N-tert-pentyloxycarbonylamino)-1,3-thiazol-4-yl]glyoxylic acidYield 84.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of ethyl 2-[2-(N-methyl-N-tert-pentyloxycarbonylamino)-1,3-thiazol-4-yl]glyoxylate (3.1 g.) in ethanol (40 ml.) was added 1 N sodium hydroxide aqueous solution (14.2 ml.) under ice-cooling and stirring, and the mixture was further stirred for 30 minutes at the same temperature. After the reaction, ethanol was distilled off from the reaction mixture below 20° C. under reduced pressure. To the residue was added water (50 ml.), and after layering with ethyl acetate, the mixture was adjusted to pH 3 with 2 N hydrochloric acid. The ethyl acetate layer was separated from the mixture, washed with water, dried over magnesium sulfate and then treated with an activated charcoal. The solvent is distilled off from the resulting ethyl acetate layer to give solid of 2-[2-(N-methyl-N-tert-pentyloxycarbonylamino)-1,3-thiazol-4-yl]glyoxylic acid (2.4 g.).

Workup

  1. temperaturecooling
  2. stirringthe mixture was further stirred for 30 minutes at the same temperature
  3. distillationwas distilled off from the reaction mixture below 20° C. under reduced pressure
  4. additionTo the residue was added water (50 ml.)
  5. customThe ethyl acetate layer was separated from the mixture
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. additiontreated with an activated charcoal
  9. distillationThe solvent is distilled off from the resulting ethyl acetate layer

Sources & evidence

ORD record
ord-4c5c218b6eca44c28e743e23da2df187
Source dataset
uspto-grants-1984_04
Patent number
US04440766

Reaction notes

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