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

HRID 2210930
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HRID 2210930 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>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]
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참가 물질

4

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%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of compound of Step 6 (0,926 g, 2.85 mmol) and trifluoroacetic acid (5.49mL, 71.3mmol) in CH2Cl2 (5.49 mL) was stirred at room temperature for 30 minutes and then concentrated in vacuo. The residue was dissolved in 1.0 N 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. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in 1.0 N KOH (7 mL)
  3. extractionextracted with ethyl acetate (4×10 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-2cc3a926bc7048a4adbfdfe2cacd984a
출처 데이터셋
uspto-grants-1995_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05461074

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