tert-Butanol → 2-(N-Boc-amino)-3-phenyl-thiophene

反応式

[C:1]1([C:7]2[CH:11]=[CH:10][S:9][C:8]=2C(O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC[N:17]([CH2:20]C)CC.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1.[C:39]([OH:43])([CH3:42])([CH3:41])[CH3:40]>>[C:39]([O:43][C:20](=[O:29])[NH:17][C:8]1[S:9][CH:10]=[CH:11][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([CH3:42])([CH3:41])[CH3:40]

参加物

反応物 4

HCID 6386tert-Butanol

HCID 8471Triethylamine

HCID 199401P,P-Diphenylphosphinic azide

HCID 25176253-phenylthiophene-2-carboxylic Acid

生成物 1

HCID 589118012-(N-Boc-amino)-3-phenyl-thiophene収率 45%

反応条件

温度: 85 °C

実験手順

3-Phenyl-thiophene-2-carboxylic acid (200 mg, 979 μmol), NEt3 (99.1 mg, 136 μL, 979 μmol) and diphenylphosphoryl azide (275 mg, 215 μL, 999 μmol) were dissolved in tert-BuOH. The solution was stirred at 85° C. for 5 h followed by RT overnight. The formed suspension was filtered and the filter cake was washed with a small amount of tert-BuOH. The filtrate was diluted with EtOAc, washed with H2O and brine. The organic layers were dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (0% to 18% EtOAc in n-heptane) to give the title compound as a yellow solid (0.122 g, 45%). MS (ESI): m/z=276.2 [M+H]+.