Ethyl bromopyruvate → Ethyl 2-ethyl-1,3-thiazole-4-carboxylate

HRID 1255285노트

반응식

HRID 1255285 반응식
Br[CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:10](=[S:14])([NH2:13])[CH2:11][CH3:12].ClC1C=CC(CO)=CC=1CCO>C(O)C>[CH2:11]([C:10]1[S:14][CH:2]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:13]=1)[CH3:12]

참가 물질

5

반응물 3

HCID 66144Ethyl bromopyruvateHCID 2760628PropanethioamideHCID 579893372-(2-Chloro-5-(hydroxymethyl)phenyl)ethanol

생성물 1

HCID 15056276Ethyl 2-ethyl-1,3-thiazole-4-carboxylate

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Ethyl 3-bromo-2-oxopropanoate (24.7 mL) was added dropwise over 10 min to a solution of propanethioamide [Carboxylic Acid 1, step a] (15.8 g) in ethanol (150 mL) at 0-10° C. under nitrogen. When the addition was complete the mixture was stirred at ambient temperature for 18 hours. The mixture was concentrated in vacuo, the residue diluted with water and extracted into ethyl acetate (×3). The combined extracts were washed with brine, dried over magnesium sulfate, filtered and the solvent removed. The crude product was purified by flash silica chromatography, elution gradient 10, 15 and 20% ethyl acetate in isohexane. Fractions containing the product were evaporated to dryness to afford the subtitled compound as a pale green solid. Yield 16.0 g.

후처리

  1. additionWhen the addition
  2. concentrationThe mixture was concentrated in vacuo
  3. additionthe residue diluted with water
  4. extractionextracted into ethyl acetate (×3)
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent removed
  9. customThe crude product was purified by flash silica chromatography, elution gradient 10, 15 and 20% ethyl acetate in isohexane
  10. additionFractions containing the product
  11. customwere evaporated to dryness

출처 및 근거

ORD 기록
ord-2f77c5702d7549b9844cfb470d4555d6
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455483B2

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