Tert-Butyl nitrite → tert-Butyl 4-azido-3-iodobenzylcarbamate

HRID 1961487노트

반응식

HRID 1961487 반응식
[NH2:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][C:3]=1[I:17].N(OC(C)(C)C)=O.[Si]([N:29]=[N+:30]=[N-])(C)(C)C>CC#N>[N:1]([C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][C:3]=1[I:17])=[N+:29]=[N-:30]

참가 물질

5

반응물 3

HCID 10906Tert-Butyl nitriteHCID 78378AzidotrimethylsilaneHCID 10383091tert-Butyl 4-amino-3-iodobenzylcarbamate

생성물 1

HCID 86661980tert-Butyl 4-azido-3-iodobenzylcarbamate수율 87.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
0 °C

실험 절차

tert-Butyl 4-amino-3-iodobenzylcarbamate (1.0 g, 2.87 mmol) was dissolved in CH3CN (6.0 ml). The solution was cooled to 0° C., tert-butyl nitrite (444.3 mg, 4.30 mmol) and TMS azide (397.1 mg, 3.45 mmol) were added. The mixture was then stirred at r.t for 2.0 h. The solvents were removed under vacuum and the residue purified by flash chromatography (Pet. Ether/EtOAc 85:15) affording 936 mg (87%) of the title compound.

후처리

  1. customThe solvents were removed under vacuum
  2. customthe residue purified by flash chromatography (Pet. Ether/EtOAc 85:15)

출처 및 근거

ORD 기록
ord-f1d7edcee4fb4b16bc6067874f8b8fdd
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415333B2

반응 노트

불러오는 중…