Ethyl bromoacetate → Ethyl trans-3-amino-4-oxo-2-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate

HRID 345142노트

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HRID 345142 반응식
[NH2:1][C@@H:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[S:4][C@H:3]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[H-].[Na+].Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>CN(C)C=O>[NH2:1][C@@H:2]1[C:8](=[O:9])[N:7]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[S:4][C@H:3]1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

참가 물질

5

반응물 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 13490514HCID 13490514, 화합물

생성물 1

HCID 14648534Ethyl trans-3-amino-4-oxo-2-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
10 °C

실험 절차

In 700 ml of dimethylformamide is dissolved 54.8 g of trans-3-amino-2-phenyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one. To this solution is added 8.8 g of 60% sodium hydride under ice-cooling. The reaction temperature is gradually elevated to room temperature, and the mixture is stirred for 1.5 hours. After the reaction mixture is again cooled to about 10° C., 100 ml of a dimethylformamide solution containing 25.5 ml of ethyl bromoacetate is added dropwise. After the reaction temperature is elevated again to room temperature, the mixture is stirred for 5 hours and then concentrated under reduced pressure. By adding ice-water and chloroform to the residue, the organic substance is extracted. After the chloroform layer is washed with water and dried, the solvent is distilled off under reduced pressure. By adding a mixed solution of isopropyl ether and isopropyl alcohol to the residue, the crystallization is effected. The resulting crystals are collected by filtration to give 37 g of ethyl trans-3-amino-4-oxo-2-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate.

후처리

  1. temperaturecooling
  2. customis gradually elevated to room temperature
  3. additionis added dropwise
  4. customis elevated again to room temperature
  5. stirringthe mixture is stirred for 5 hours
  6. concentrationconcentrated under reduced pressure
  7. additionBy adding ice-water and chloroform to the residue
  8. extractionthe organic substance is extracted
  9. washAfter the chloroform layer is washed with water
  10. customdried
  11. distillationthe solvent is distilled off under reduced pressure
  12. additionBy adding a mixed solution of isopropyl ether and isopropyl alcohol to the residue
  13. customthe crystallization
  14. filtrationThe resulting crystals are collected by filtration

출처 및 근거

ORD 기록
ord-37c78658c1734910989d211be8e3090f
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05055464

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