Hydrogen Bromide → [3-Bromo-1-(4-nitro-benzyl)-2-oxo-propyl]-carbamic acid tert-butyl ester

HRID 60052

反応式

HRID 60052 の反応式
[C:1]([O:5][C:6](=[O:24])[NH:7][CH:8]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)[C:9](=[O:13])[CH:10]=[N+]=[N-])([CH3:4])([CH3:3])[CH3:2].[BrH:25]>C1COCC1>[C:1]([O:5][C:6](=[O:24])[NH:7][CH:8]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)[C:9](=[O:13])[CH2:10][Br:25])([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 260Hydrogen BromideHCID 72739076[3-Diazo-1-(4-nitrobenzyl)-2-oxo-propyl]-carbamic acid tert-butyl ester

生成物 1

HCID 76068232[3-Bromo-1-(4-nitro-benzyl)-2-oxo-propyl]-carbamic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a 0° C. solution of [3-diazo-1-(4-nitrobenzyl)-2-oxo-propyl]carbamic acid tert-butyl ester, 50, (0.350 g, 1.04 mmol) in THF (5 mL) is added dropwise 48% aq. HBr (0.14 mL, 1.25 mmol). The reaction mixture is stirred at 0° C. for 1.5 hours and quenched at 0° C. with saturated aqueous Na2CO3. The mixture is extracted with EtOAc (3×25 mL) and the combined organic extracts are washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to afford 0.400 g of the desired product that is used in the next step without further purification. 1H NMR (300 MHz, CDCl3) δ 8.20 (d, J=8.4 Hz, 2H), 7.39 (d, J=8.4 Hz, 2H), 5.06 (d, J=7.8 Hz, 1H), 4.80 (q, J=6.3 Hz, 1H), 4.04 (s, 2H), 1.42 (s, 9H).

後処理

  1. customquenched at 0° C. with saturated aqueous Na2CO3
  2. extractionThe mixture is extracted with EtOAc (3×25 mL)
  3. washthe combined organic extracts are washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-7dbed3d9fb2c4e70b815de9892df3388
出典データセット
uspto-grants-2016_09
特許番号
US09440963B2

関連ノート

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