Benzophenone → N-(Diphenylmethylene)glycine tert-butyl ester

HRID 387415

反応式

HRID 387415 の反応式
[NH2:1][CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[C:10]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:11]1([C:10](=[N:1][CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

参加物

5

反応物 3

HCID 3102BenzophenoneHCID 6101p-Toluenesulfonic acidHCID 151417Glycine tert-butyl ester

生成物 1

HCID 688171N-(Diphenylmethylene)glycine tert-butyl ester収率 48.8%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
15 °C

実験手順

A solution of t-butyl 2-aminoacetate (113.7 g, 866.8 mmol, 1.0 equiv) in toluene (1000 mL) was combined with benzophenone (157.9 g, 866.5 mmol, 1.0 equiv) and 4-methylbenzenesulfonic acid (14.9 g, 86.5 mmol, 0.1 equiv). The resulting solution was heated to reflux overnight. The mixture was then concentrated in vacuo to 600 mL. The mixture was cooled to 15° C. with a water/ice bath. The product precipitated and the solids were collected by filtration. The solids was washed with petroleum ether (5×150 mL) to yield t-butyl 2-(diphenylmethyleneamino)acetate (125 g) as a white solid.

後処理

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux overnight
  3. concentrationThe mixture was then concentrated in vacuo to 600 mL
  4. customThe product precipitated
  5. filtrationthe solids were collected by filtration
  6. washThe solids was washed with petroleum ether (5×150 mL)

出典と根拠

ORDレコード
ord-6ecd3f1a47434f90bf24de5f5ac70dd4
出典データセット
uspto-grants-2013_02
特許番号
US08372984B2

関連ノート

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