Ethanol → (2-t-Pentyloxycarbonylamino-1,3-thiazol-4-yl)glyoxylic acid

HRID 648397Notes

Reaction equation

HRID 648397 reaction equation
[C:1]([O:6][C:7]([NH:9][C:10]1[S:11][CH:12]=[C:13]([C:15](=[O:21])[C:16]([O:18]CC)=[O:17])[N:14]=1)=[O:8])([CH2:4][CH3:5])([CH3:3])[CH3:2].C(O)C.[OH-].[Na+]>O>[C:1]([O:6][C:7]([NH:9][C:10]1[S:11][CH:12]=[C:13]([C:15](=[O:21])[C:16]([OH:18])=[O:17])[N:14]=1)=[O:8])([CH2:4][CH3:5])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 19978748Ethyl 2-(2-t-pentyloxycarbonylamino-1,3-thiazol-4-yl)glyoxylate

Product 1

HCID 19978737(2-t-Pentyloxycarbonylamino-1,3-thiazol-4-yl)glyoxylic acidYield 68.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 2-(2-tert-pentyloxycarbonylamino-1,3-thiazol-4-yl)glyoxylate (2.8 g.) and ethanol (10 ml.) was mixed with a solution of sodium hydroxide (0.54 g.) in water (20 ml.), and the mixture was stirred for 1 hour at room temperature. After the reaction, a small amount of ethanol was distilled off. The remaining reaction mixture was washed with diethyl ether and then the aqueous layer was separated therefrom. To the aqueous layer was added ethyl acetate, and the mixture was adjusted to pH 1 to 2 with 10% hydrochloric acid and then the ethyl acetate layer was separated therefrom. The ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and then treated with activated charcoal. The solvent was distilled off from the ethyl acetate layer to give yellow brown powder of 2-(2-tert-pentyloxycarbonylamino-1,3-thiazol-4-yl)glyoxylic acid (1.75 g.).

Workup

  1. customAfter the reaction
  2. distillationa small amount of ethanol was distilled off
  3. customThe remaining reaction mixture
  4. washwas washed with diethyl ether
  5. customthe aqueous layer was separated
  6. additionTo the aqueous layer was added ethyl acetate
  7. customthe ethyl acetate layer was separated
  8. washThe ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride
  9. dry with materialdried over magnesium sulfate
  10. additiontreated with activated charcoal
  11. distillationThe solvent was distilled off from the ethyl acetate layer

Sources & evidence

ORD record
ord-58ed63f24b004e66a6151ce6cbb1b9d2
Source dataset
uspto-grants-1983_10
Patent number
US04411898

Reaction notes

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