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

HRID 1720890
ノート
印刷プレビュー

反応式

HRID 1720890 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>C(Cl)Cl>[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

4

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%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

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 CH2Cl2 (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. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in 1.0N KOH (7 mL)
  3. extractionextracted with ethyl acetate (4×10 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-181e7cff56eb41469eedc4e32c0ee6f7
出典データセット
uspto-grants-1996_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05508295

反応ノート

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