Iodine → tert-Butyl 4-amino-3-iodobenzylcarbamate

HRID 966532ノート

反応式

HRID 966532 の反応式
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Ca+2].[I:22]I>CO>[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([NH2:15])=[C:13]([I:22])[CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 807IodineHCID 10112Calcium CarbonateHCID 2756041tert-butyl N-[(4-aminophenyl)methyl]carbamate

生成物 1

HCID 10383091tert-Butyl 4-amino-3-iodobenzylcarbamate収率 47%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a mixture of (4-amino-benzyl)-carbamic acid tert-butyl ester (4.8 g, 21.6 mmol) and calcium carbonate (2.7 g, 27 mmol) in methanol (60 mL) was added iodine (5.5 g, 21.6 mmol) in portions. The mixture was heated at reflux overnight and then concentrated in vacuo to give a dark brown residue, which was partitioned between ethyl acetate and saturated sodium bisulfite solution. The organic phase was washed with water and brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to give a residue, which was purified by chromatography (5%-20% ethyl acetate in hexanes) to give 3.5 g (47%) of the desired product as a brown semi-solid. MS(APCI+): m/z 349.1 (MH+).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated in vacuo
  4. customto give a dark brown residue, which
  5. customwas partitioned between ethyl acetate and saturated sodium bisulfite solution
  6. washThe organic phase was washed with water and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated in vacuo
  10. customto give a residue, which
  11. customwas purified by chromatography (5%-20% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-0e25684666ea4fcb97dd193a43e2935f
出典データセット
uspto-grants-2005_10
特許番号
US06951848B2

反応ノート

読み込み中…