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Ethanol → HCID 69348337, 화합물

HRID 336337
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HRID 336337 반응식
[N@:1]1([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:3][CH:2]1[C:4]([O:6][CH3:7])=[O:5].B(F)(F)F.[CH3:22][CH2:23][O:24]CC.C(O)C>ClCCl>[CH2:11]([O:10][C:8]([NH:1][C@H:2]([C:4]([O:6][CH3:7])=[O:5])[CH2:3][O:24][CH2:23][CH3:22])=[O:9])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 702EthanolHCID 8000Boron trifluoride etherateHCID 42559581-Benzyl 2-methyl aziridine-1,2-dicarboxylate

생성물 1

HCID 69348337HCID 69348337, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of (S)-1-benzyl 2-methyl aziridine-1,2-dicarboxylate (prepared according to the literature procedure: Org. Biomol. Chem., 2005, 3, 3357, 2.7 g, 11.4 mmol) in dichloromethane (30 mL), boron trifluoride etherate (0.01 mL, 0.11 mmol) was added at 0° C. followed by absolute ethanol (1.05 g, 22.9 mmol). The reaction mixture was stirred at room temperature for an hour, after which the solution was quenched with saturated bicarbonate solution (2 mL), extracted with dichloromethane (3×25 mL), organic layers were washed with water (25 mL), brine solution (25 mL) and dried over sodium sulfate. The removal of solvents afforded crude product, which was purified by silica gel column chromatography using a gradient of ethyl acetate in pet. ether. Yield: 2.0 g (63%). 1H NMR (400 MHz, DMSO-d6) δ: 1.08 (t, 3H), 3.38-3.46 (m, 2H), 3.57-3.63 (m, 2H), 3.70 (s, 3H), 4.26-4.31 (m, 1H), 5.04 (s, 2H), 7.30-7.39 (m, 5H), 7.73 (d, 1H).

후처리

  1. customafter which the solution was quenched with saturated bicarbonate solution (2 mL)
  2. extractionextracted with dichloromethane (3×25 mL), organic layers
  3. washwere washed with water (25 mL), brine solution (25 mL)
  4. dry with materialdried over sodium sulfate
  5. customThe removal of solvents
  6. customafforded crude product, which
  7. customwas purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-78763c612a604196890b5813be9f7292
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08889671B2

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