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

HRID 710948
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HRID 710948 반응식
[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[N:32]1[C:36](=[O:37])[C:35]2=[CH:38][CH:39]=[CH:40][CH:41]=[C:34]2[C:33]1=[O:42].N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9][O:10][N:32]1[C:36](=[O:37])[C:35]2[C:34](=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:33]1=[O:42])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

6

반응물 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamate

생성물 1

HCID 18929164tert-Butyl (2-((1,3-dioxoisoindolin-2-yl)oxy)ethyl)carbamate수율 85.2%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

tert-Butyl(2-hydroxyethyl)carbamate (1.61 g, 10.0 mmol) was stirred under an argon atmosphere at room temperature with dehydrated tetrahydrofuran (50 mL). Then, triphenylphosphine (2.75 g) and N-hydroxyphthalimide (Pht-OH, 1.71 g) were added. After the reaction mixture was under ice cooling, diethyl azodicarboxylate (DEAD, 1.82 g) was added dropwise gradually, followed by stirring at room temperature for 24 hours. After completion of the reaction, the residue resulting from distilling off the solvent under reduced pressure was subjected to silica gel column chromatography (hexane/ethyl acetate=4/1→1/1) to afford 2.61 g of the title compound (yield 85.2%).

후처리

  1. customAfter completion of the reaction
  2. customthe residue resulting
  3. distillationfrom distilling off the solvent under reduced pressure

출처 및 근거

ORD 기록
ord-43e05f68a2fa428fbf746726571a35dd
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09181250B2

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