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

HRID 1961487ノート

反応式

HRID 1961487 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 86661980tert-Butyl 4-azido-3-iodobenzylcarbamate収率 87.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-f1d7edcee4fb4b16bc6067874f8b8fdd
出典データセット
uspto-grants-2013_04
特許番号
US08415333B2

反応ノート

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