N-Hydroxyphthalimide → Benzyl (2-((1,3-dioxoisoindolin-2-yl)oxy)ethyl)carbamate

HRID 749076노트

반응식

HRID 749076 반응식
[OH:1][CH2:2][CH2:3][NH:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O[N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C(OCC)(=O)C>[CH2:7]([O:6][C:5]([NH:4][CH2:3][CH2:2][O:1][N:16]1[C:17](=[O:26])[C:18]2=[CH:25][CH:24]=[CH:23][CH:22]=[C:19]2[C:20]1=[O:21])=[O:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

참가 물질

7

반응물 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 280458benzyl N-(2-hydroxyethyl)carbamate

생성물 1

HCID 13983475Benzyl (2-((1,3-dioxoisoindolin-2-yl)oxy)ethyl)carbamate수율 91.1%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of benzyl N-(2-hydroxyethyl)carbamate (5.9 g, 30 mmol), N-hydroxyphthalimide (4.9 g, 30 mmol), and triphenylphosphine (7.9 g, 30 mmol) in tetrahydrofuran (100 mL) was added diethyl azodicarboxylate (5.2 g, 30 mmol). The reaction mixture was stirred at room temperature overnight. Ethyl acetate (200 mL) was added, the solution washed with saturated NaHCO3 (2×100 mL) and brine (100 mL), and dried over Na2SO4. After evaporating the solvent, the residue was purified by flash column chromatography (methylene chloride to 4% ethyl acetate in methylene chloride) to give the title compound as a white solid (9.3 g, 91%). 1H-NMR (300 MHz, CDCl3) δ 7.84 (m, 2H), 7.78 (m, 2H), 7.37 (m, 5H), 5.97 (br s, 1H), 5.14 (s, 2H), 4.27 (t, J=4.9 Hz, 2H), 3.51 (q, J=5.2 Hz, 2H).

후처리

  1. washthe solution washed with saturated NaHCO3 (2×100 mL) and brine (100 mL)
  2. dry with materialdried over Na2SO4
  3. customAfter evaporating the solvent
  4. customthe residue was purified by flash column chromatography (methylene chloride to 4% ethyl acetate in methylene chloride)

출처 및 근거

ORD 기록
ord-5285b88d23e5487ab8d5ccd8adfe07dd
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07402586B2

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