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

HRID 710949
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HRID 710949 반응식
[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9]Br)([CH3:4])([CH3:3])[CH3:2].C(#N)C.[OH:15][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]>C(N(CC)CC)C>[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9][O:15][N:16]1[C:20](=[O:21])[C:19]2[C:18](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:17]1=[O:26])([CH3:4])([CH3:3])[CH3:2]
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참가 물질

5

반응물 3

HCID 6342AcetonitrileHCID 10665N-HydroxyphthalimideHCID 4103526tert-Butyl N-(2-bromoethyl)carbamate

생성물 1

HCID 18929164tert-Butyl (2-((1,3-dioxoisoindolin-2-yl)oxy)ethyl)carbamate수율 65.7%

시약·촉매·용매 1

HCID 8471Triethylamine용매

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온도
70 °C

실험 절차

tert-Butyl(2-bromoethyl)carbamate (5.00 g, 23.5 mmol) was stirred under an argon atmosphere at room temperature with acetonitrile (74 mL). Then, N-hydroxyphthalimide (Pht-OH, 3.83 g) and triethylamine (5.64 g) were added, followed by stirring the reaction mixture at 70° C. for 24 hours. After completion of the reaction, the reaction solution was concentrated, followed by diluting with ethyl acetate and washing with 0.5M hydrochloric acid and saturated sodium bicarbonate aqueous solution, and the organic layer was dried over magnesium sulfate, to the residue resulting from distilling off the solvent under reduced pressure was added ethyl acetate (10 ml), followed by adding hexane, thereby 4.72 g of the title compound was afforded (yield 65.7%). The instrumental data were consistent with those of the compound of Reference Example 7.

후처리

  1. customAfter completion of the reaction
  2. concentrationthe reaction solution was concentrated
  3. additionby diluting with ethyl acetate
  4. washwashing with 0.5M hydrochloric acid and saturated sodium bicarbonate aqueous solution
  5. dry with materialthe organic layer was dried over magnesium sulfate, to the residue
  6. customresulting
  7. distillationfrom distilling off the solvent under reduced pressure
  8. additionwas added ethyl acetate (10 ml)
  9. additionby adding hexane

출처 및 근거

ORD 기록
ord-c84a4264df3b4b6a889c464ec1b83a28
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09181250B2

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