Ethanol → Ethyl 2-(pivaloyloxymethyl)thiazole-4-carboxylate

HRID 2390540Notes

Reaction equation

HRID 2390540 reaction equation
[C:1]([O:7][CH2:8][C:9]([NH2:11])=[S:10])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].Br[CH2:13][C:14](=O)[C:15]([OH:17])=[O:16].[CH3:19][CH2:20]O>>[C:1]([O:7][CH2:8][C:9]1[S:10][CH:13]=[C:14]([C:15]([O:17][CH2:19][CH3:20])=[O:16])[N:11]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 3

HCID 702EthanolHCID 70684Bromopyruvic AcidHCID 27821132-Amino-2-thioxoethyl 2,2-dimethylpropanoate

Product 1

HCID 67025585Ethyl 2-(pivaloyloxymethyl)thiazole-4-carboxylate

Procedure

2-Amino-2-thioxoethyl pivalate (3.0 g, 17.12 mmol) and 3-bromo-2-oxopropanoic acid (3.14 g, 18.83 mmol) were dissolved in EtOH (20 mL), 4 Å molecular sieves added and the reaction mixture heated at reflux for 20 h then cooled to RT, filtered, washed with EtOH and evaporated in vacuo. The residual semi solid was treated with 50% EtOAc/DCM and the resulting light brown solid filtered off. The filtrate was evaporated in vacuo and the residue purified by chromatography on silica with 20% EtOAc/isohexane as eluent to afford the sub-title compound as a pale yellow oil. Yield: 2.47 g

Workup

  1. addition4 Å molecular sieves added
  2. temperaturethe reaction mixture heated
  3. temperatureat reflux for 20 h
  4. filtrationfiltered
  5. washwashed with EtOH
  6. customevaporated in vacuo
  7. additionThe residual semi solid was treated with 50% EtOAc/DCM
  8. filtrationthe resulting light brown solid filtered off
  9. customThe filtrate was evaporated in vacuo
  10. customthe residue purified by chromatography on silica with 20% EtOAc/isohexane as eluent

Sources & evidence

ORD record
ord-253291dec6f7448ebbde3aaf6b1ea19f
Source dataset
uspto-grants-2012_09
Patent number
US08273774B2

Reaction notes

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