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Ethanol → (S)-3-Amino-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetic Acid Ethyl Ester

HRID 617894
ノート
印刷プレビュー

反応式

HRID 617894 の反応式
[NH2:1][C@H:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[N:4]([CH2:13][C:14]([O:16][C:17](C)(C)[CH3:18])=[O:15])[C:3]1=[O:21].C1(C)C=CC(S(O)(=O)=O)=CC=1.O.C(O)C>C1(C)C=CC=CC=1>[NH2:1][C@H:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[N:4]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:3]1=[O:21]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 702EthanolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 63506241,1-Dimethylethyl ((3S)-3-amino-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)acetate

生成物 1

HCID 13243526(S)-3-Amino-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetic Acid Ethyl Ester収率 79.7%

試薬・触媒・溶媒 1

HCID 1140
Toluene
溶媒

実験手順

5.0 g of tert-butyl (3S)-3-amino-2,3,4,5-tetrahydro-2-oxo-1H-benzazepine-1-acetate (preparation see Example 3E)) and 3.75 g of p-toluenesulfonic acid were boiled in a water separator for 2.5 hours in 80 ml of toluene. A total of 200 ml of ethanol was then added in portions, and the resulting reaction mixture was refluxed for 3.5 hours. The mixture was then concentrated in vacuo, and the residue was taken up with dichloromethane. The mixture was shaken with ice-cold sodium carbonate solution, and the organic phase was washed with water until neutral. The organic phase was dried over sodium sulfate, evaporated in vacuo and the residue which remained was dried. 3.6 g of ethyl (3S)-3-amino-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetate were obtained, m.p.=106.5°-108° C.; IR: 3350, 3300, 2930, 1735, 1660 cm-1 (film); [α]D20 =-288.4° (c=0.5 in methanol).

後処理

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for 3.5 hours
  3. concentrationThe mixture was then concentrated in vacuo
  4. washthe organic phase was washed with water until neutral
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. customevaporated in vacuo
  7. customthe residue which remained was dried

出典と根拠

ORDレコード
ord-6d602bbc1eb84a78a39fe1d7393bc841
出典データセット
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05952327

反応ノート

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