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Trifluoroacetic acid → (4s,5r,6s)-6-Amino-7-cyclohexyl-4,5-dihydroxy-1-heptyne

HRID 6079
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반응식

HRID 6079 반응식
C(OC([NH:8][C@@H:9]([CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[C@@H:10]([OH:16])[C@@H:11]([OH:15])[CH2:12][C:13]#[CH:14])=O)(C)(C)C.FC(F)(F)C(O)=O>>[NH2:8][C@@H:9]([CH2:17][CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1)[C@@H:10]([OH:16])[C@@H:11]([OH:15])[CH2:12][C:13]#[CH:14]
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참가 물질

3

반응물 2

HCID 6422Trifluoroacetic acidHCID 15281986(4S,5R,6S)-N-[(tert-Butyloxy) carbonyl]-6-amino-7-cyclohexyl-4,5-dihydroxyhept-1-yne

생성물 1

HCID 15281987(4s,5r,6s)-6-Amino-7-cyclohexyl-4,5-dihydroxy-1-heptyne수율 104.3%

실험 절차

A solution of compound of Step 6 (0.926 g, 2.85 mmol) and trifluoroacetic acid (5.49 mL, 71.3 mmol) in CH2Cl12 (5.49 mL) was stirred at room temperature for 30 minutes and then concentrated in vacuo. The residue was dissolved in 1.0N KOH (7 mL) and extracted with ethyl acetate (4×10 mL). The combined organic layers were dried over MgSO4 and then concentrated to give the title amine as an off-white solid (0.67 g, 100% yield). 1H and 13C NMR spectral data were consistent with the proposed structure.

후처리

  1. concentration
concentrated in vacuo
  • dissolutionThe residue was dissolved in 1.0N KOH (7 mL)
  • extractionextracted with ethyl acetate (4×10 mL)
  • dry with materialThe combined organic layers were dried over MgSO4
  • concentrationconcentrated
  • 출처 및 근거

    ORD 기록
    ord-e0171f7df0ec444092af546b5b14249f
    출처 데이터셋
    uspto-grants-1993_09
    DOI
    10.6084/m9.figshare.5104873.v1
    특허 번호
    US05246969

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