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

HRID 617894Notes

Reaction equation

HRID 617894 reaction equation
[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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-6d602bbc1eb84a78a39fe1d7393bc841
Source dataset
uspto-grants-1999_09
Patent number
US05952327

Reaction notes

Loading…