Trifluoroacetic acid → 3-(2-(Methylthio)ethyl)piperazin-2-one

HRID 484970

반응식

HRID 484970 반응식
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][NH:18][C:17](=[O:21])[CH:16]1[CH2:22][CH2:23][S:24][CH3:25])=O)(C)(C)C>C(SCC)C>[CH3:25][S:24][CH2:23][CH2:22][CH:16]1[NH:15][CH2:20][CH2:19][NH:18][C:17]1=[O:21]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 233196714-t-Butoxycarbonyl-3-[2-(methylthio)ethyl]piperazinone

생성물 1

HCID 135204093-(2-(Methylthio)ethyl)piperazin-2-one

시약·촉매·용매 1

HCID 9609Ethyl sulfide용매

실험 절차

Trifluoroacetic acid (30 ml.) is added at 0° to a stirred solution of 4-t-butoxycarbonyl-3-[2-(methylthio)ethyl]piperazinone (XVII, Example 43, 2.6 g., 0.0095 mole) in diethyl sulfide (20 ml.). After 1 hour the solvents are removed and the residual oil is partitioned between chloroform (300 ml.) and 5N sodium hydrochloride solution (10 ml.). The chloroform is washed with water (2×10 ml.) and the chloroform is removed under reduced pressure. The residual oil is chromatographed on silica gel eluted with methanol:chloroform (1:9), the appropriate fractions are pooled and concentrated to give a solid which upon recrystallization from ethyl acetate:SSB gives the title compound, m.p. 68°-70°.

후처리

  1. customAfter 1 hour the solvents are removed
  2. customthe residual oil is partitioned between chloroform (300 ml.) and 5N sodium hydrochloride solution (10 ml.)
  3. washThe chloroform is washed with water (2×10 ml.)
  4. customthe chloroform is removed under reduced pressure
  5. customThe residual oil is chromatographed on silica gel
  6. washeluted with methanol:chloroform (1:9)
  7. concentrationconcentrated
  8. customto give a solid which
  9. customupon recrystallization from ethyl acetate

출처 및 근거

ORD 기록
ord-4ff507300b57492aba03500969846b14
출처 데이터셋
uspto-grants-1985_08
특허 번호
US04534897

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