Bromide ion → (S)-2-(4-bromobenzyl)amino-3-methylbutyric acid

HRID 12592

反応式

HRID 12592 の反応式
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4](S([O-])(=O)=O)=[CH:3][CH:2]=1.[NH2:12][C@H:13]([C:17]([OH:19])=[O:18])[CH:14]([CH3:16])[CH3:15].C[Si](C)(C)N[Si](C)(C)C.C(N(C(C)C)CC)(C)C.[Br-:38]>C(Cl)Cl>[Br:38][C:4]1[CH:5]=[CH:6][C:1]([CH2:11][NH:12][C@H:13]([C:17]([OH:19])=[O:18])[CH:14]([CH3:16])[CH3:15])=[CH:2][CH:3]=1

参加物

7

反応物 5

HCID 259Bromide ionHCID 6287L-ValineHCID 13838HexamethyldisilazaneHCID 81531DiisopropylethylamineHCID 85570p-Toluenesulfonate

生成物 1

HCID 11673643(S)-2-(4-bromobenzyl)amino-3-methylbutyric acid収率 89%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
22.5 °C

実験手順

To a suspension of 10 g (34.6 mmol) of p-toluenesulphonate of L-valine in 100 mL of CH2Cl2 is added at 20-25° C. and under nitrogen atmosphere 8.0 mL (38 mmol) of 1,1,1,3,3,3-hexamethyldisilazane. After shaking the mixture at 20-25° C. for one hour, 13.2 mL (76 mmol) of diisopropylethylamine and 8.64 g (34.6 mmol) of 4-bromobenzylo bromide are added and heated at reflux. When all the 4-bromobenzylo bromide has been consumed, the solvent is evaporated off at low pressure, 100 mL of water is added and after 1 h at 0° C. the solid is filtered and dried in an air oven at 40° C. to provide 8.8 g (89%) of N-(4-bromobenzyl)-L-valine.

後処理

  1. temperatureheated
  2. temperatureat reflux
  3. customWhen all the 4-bromobenzylo bromide has been consumed
  4. customthe solvent is evaporated off at low pressure, 100 mL of water
  5. additionis added and after 1 h at 0° C. the solid
  6. filtrationis filtered
  7. customdried in an air oven at 40° C.

出典と根拠

ORDレコード
ord-5759d37bf2144098891bfd299ba656fc
出典データセット
uspto-grants-2010_06
特許番号
US07728021B2

関連ノート

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