Ethanol → 2-(5-Acetyl-furan-2-ylmethyl)-thiazole-4-carboxylic acid ethyl ester

HRID 1189428Notes

Reaction equation

HRID 1189428 reaction equation
N#N.[CH3:3][C:4]1([C:9]2[O:13][C:12]([CH2:14][C:15]([NH2:17])=[S:16])=[CH:11][CH:10]=2)[O:8]CCO1.C([CH:20](Br)[C:21](=O)[C:22]([O-:24])=[O:23])C.[CH2:27](O)[CH3:28]>>[CH2:27]([O:24][C:22]([C:21]1[N:17]=[C:15]([CH2:14][C:12]2[O:13][C:9]([C:4](=[O:8])[CH3:3])=[CH:10][CH:11]=2)[S:16][CH:20]=1)=[O:23])[CH3:28]

Participants

5

Reactant 4

HCID 702EthanolHCID 947NitrogenHCID 21948992EthylbromopyruvateHCID 866649202-[5-(2-Methyl-[1,3]dioxolan-2-yl)-furan-2-yl]-thioacetamide

Product 1

HCID 671284872-(5-Acetyl-furan-2-ylmethyl)-thiazole-4-carboxylic acid ethyl ester

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-[5-(2-methyl-[1,3]dioxolan-2-yl)-furan-2-yl]-thioacetamide (3.20 g, 14.06 mmol) and ethylbromopyruvate (2.07 mL, 14.06 mmol) in ethanol (40 mL) was stirred for 30 min at reflux. The solvent was removed under reduced pressure and the residue was dissolved in EA (150 mL) and washed with 7% aq. NaHCO3 (100 mL). The org. phase was dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (1:1 hept-EA) gave the title compound as an orange oil. TLC: rf (1:1 hept-EA)=0.24. LC-MS-conditions 02: tR=0.86 min, [M+H]+=280.30.

Workup

  1. temperatureat reflux
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in EA (150 mL)
  4. washwashed with 7% aq. NaHCO3 (100 mL)
  5. dry with materialphase was dried over MgSO4
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. customPurification of the residue by FC (1:1 hept-EA)

Sources & evidence

ORD record
ord-563b02e4c6164b63b0329504351f9bf8
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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