Hydrochloric Acid → Ethyl 2-cyclobutylthiazole-4-carboxylate

HRID 471119노트

반응식

HRID 471119 반응식
Cl.[CH:2]1([C:6]([NH:8][CH:9]([CH2:15][SH:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=O)[CH2:5][CH2:4][CH2:3]1>C(O)C>[CH:2]1([C:6]2[S:16][CH:15]=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:8]=2)[CH2:5][CH2:4][CH2:3]1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 57989145Ethyl 2-(cyclobutanecarboxamido)-3-mercaptopropanoate

생성물 1

HCID 54513950Ethyl 2-cyclobutylthiazole-4-carboxylate

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of HCl (4M in 1,4-dioxane, 3.46 mL) was added to a solution of ethyl 2-(cyclobutanecarboxamido)-3-mercaptopropanoate (example 58, step a) (3.2 g) in ethanol (20 mL) and the resulting mixture stirred overnight. The solvent was evaporated and the residue azeotroped twice with toluene. The residue was redissolved in acetonitrile (50 mL), manganese dioxide (12 g) was added and the mixture heated at reflux overnight. The reaction was filtered through a pad of Celite which was then washed with MeCN (3×100 mL). The combined filtrate and washings were evaporated and the residue was purified by silica gel chromatography eluting with 9:1 isohexane:ethyl acetate. The fractions containing product were combined and evaporated to give the subtitled compound as a clear oil. Yield 0.48 g.

후처리

  1. customThe solvent was evaporated
  2. customthe residue azeotroped twice with toluene
  3. dissolutionThe residue was redissolved in acetonitrile (50 mL)
  4. additionmanganese dioxide (12 g) was added
  5. temperaturethe mixture heated
  6. temperatureat reflux overnight
  7. filtrationThe reaction was filtered through a pad of Celite which
  8. washwas then washed with MeCN (3×100 mL)
  9. customThe combined filtrate and washings were evaporated
  10. customthe residue was purified by silica gel chromatography
  11. washeluting with 9:1 isohexane
  12. additionThe fractions containing product
  13. customevaporated

출처 및 근거

ORD 기록
ord-f5c2feef18584ad1bd8bf0b26215d5ba
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629271B2

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