Succinic anhydride → N-(3-Carboxypropanoyl)-N-methyl-glycine Benzyl Ester

HRID 1716

反応式

HRID 1716 の反応式
[CH2:1]([O:8][C:9](=[O:13])[CH2:10][NH:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14]1(=[O:20])[O:19][C:17](=[O:18])[CH2:16][CH2:15]1>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9](=[O:13])[CH2:10][N:11]([C:14](=[O:20])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 7922Succinic anhydrideHCID 7019103Benzyl 2-(methylamino)acetate

生成物 1

HCID 19356295N-(3-Carboxypropanoyl)-N-methyl-glycine Benzyl Ester収率 86.3%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of sarcosine benzyl ester (3.0 g, 30.7 mmol) and succinic anhydride (5.5 g, 30.7 mmol) in toluene (75 mL) was heated to reflux for 3 h, cooled, filtered, and the filtrate was concentrated. The residue was taken up in 5% aqueous sodium carbonate and extracted with ethyl acetate. The aqueous phase was adjusted to pH 3 with concentrated hydrochloric using Congo Red paper and extracted with ethyl acetate. The organic phase was washed with water, dried (magnesium sulfate) and concentrated to yield the title compound (7.4 g, 67.5%): TLC Rf 0.48 (silica, 9:1:1 dichloromethane:methanol:formic acid).

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. extractionextracted with ethyl acetate
  7. concentrationwith concentrated hydrochloric
  8. extractionextracted with ethyl acetate
  9. washThe organic phase was washed with water
  10. dry with materialdried (magnesium sulfate)
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-ccae603003f14fca9668b5a8da6d0d4d
出典データセット
uspto-grants-1998_03
特許番号
US05726192

関連ノート

読み込み中…