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

HRID 6079
ノート
印刷プレビュー

反応式

HRID 6079 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

3

反応物 2

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

生成物 1

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

実験手順

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.

後処理

  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
  • 出典と根拠

    ORDレコード
    ord-e0171f7df0ec444092af546b5b14249f
    出典データセット
    uspto-grants-1993_09
    DOI
    10.6084/m9.figshare.5104873.v1
    特許番号
    US05246969

    反応ノート

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