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N-[2-(tert-Butyldimethylsilanyloxymethyl)allyl]-2-diazo-N-(2,4-dimethoxybenzyl)acetamide → 5-(Tert-butyldimethylsilanyloxymethyl)-3-(2,4-dimethoxybenzyl)-3-azabicyclo[3.1.0]hexan-2-one

HRID 83575
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HRID 83575 반응식
[Si:1]([O:8][CH2:9][C:10](=[CH2:29])[CH2:11][N:12]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=1[O:27][CH3:28])[C:13](=[O:17])[CH:14]=[N+]=[N-])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C1(C(F)(F)F)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Rh+2]>[Si:1]([O:8][CH2:9][C:10]12[CH2:29][CH:14]1[C:13](=[O:17])[N:12]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=1[O:27][CH3:28])[CH2:11]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]
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참가 물질

4

반응물 1

HCID 123927604N-[2-(tert-Butyldimethylsilanyloxymethyl)allyl]-2-diazo-N-(2,4-dimethoxybenzyl)acetamide

생성물 1

HCID 894658645-(Tert-butyldimethylsilanyloxymethyl)-3-(2,4-dimethoxybenzyl)-3-azabicyclo[3.1.0]hexan-2-one수율 35.4%

시약·촉매·용매 2

HCID 21674Acetic acid, rhodium(2+) salt촉매HCID 7368(Trifluoromethyl)benzene용매

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온도
50 °C

실험 절차

Under argon atmosphere, to a solution of N-[2-(tert-butyldimethylsilanyloxymethyl)allyl]-2-diazo-N-(2,4-dimethoxybenzyl)acetamide (43 mg) in benzotrifluoride (0.4 ml) was added rhodium (II) acetate dimer dihydrate (2.4 mg) at room temperature, and the mixture was stirred at 50° C. for 24 hours. This reaction mixture was concentrated under reduced pressure, the resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1) to give the titled compound (14.2 mg).

후처리

  1. concentrationThis reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1)

출처 및 근거

ORD 기록
ord-b73ca5ad23e647a18625f7baa899dd65
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08846746B2

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