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

HRID 387415

반응식

HRID 387415 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
15 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6ecd3f1a47434f90bf24de5f5ac70dd4
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372984B2

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