Ethyl 2-(cyclopentanecarboxamido)-3-mercaptopropanoate → Ethyl 2-cyclopentyl-4,5-dihydrothiazole-4-carboxylate

HRID 1689352노트

반응식

HRID 1689352 반응식
[CH:1]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][CH2:2]1>C1(C)C=CC=CC=1>[CH:1]1([C:6]2[S:16][CH2:15][CH:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

3

반응물 1

HCID 57989260Ethyl 2-(cyclopentanecarboxamido)-3-mercaptopropanoate

생성물 1

HCID 57989100Ethyl 2-cyclopentyl-4,5-dihydrothiazole-4-carboxylate

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Tosic acid monohydrate (0.78 g) was added to a solution of ethyl 2-(cyclopentanecarboxamido)-3-mercaptopropanoate (example 59, step a) (5 g) in toluene (40 mL). The resulting mixture was heated at reflux under Dean and Stark conditions for 6 h. The reaction was allowed to cool, then the toluene solution was washed with saturated sodium bicarbonate solution (20 mL) and the solvent evaporated. The residue was azeotroped with toluene. The resulting white solid 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 3.2 g.

후처리

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux under Dean and Stark conditions for 6 h
  3. temperatureto cool
  4. washthe toluene solution was washed with saturated sodium bicarbonate solution (20 mL)
  5. customthe solvent evaporated
  6. customThe residue was azeotroped with toluene
  7. customThe resulting white solid was purified by silica gel chromatography
  8. washeluting with 9:1 isohexane
  9. additionThe fractions containing product
  10. customevaporated

출처 및 근거

ORD 기록
ord-0020479e9bdf4edbb13025ba781bf8ee
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148373B2

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