Ethyl bromoacetate → HCID 67931189, compound

HRID 345149Notes

Reaction equation

HRID 345149 reaction equation
Br.[NH2:2][C@@H:3]1[C:9](=[O:10])[NH:8][C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[S:5][C@H:4]1[C:15]1[S:16][CH:17]=[CH:18][CH:19]=1.[H-].[Na+].Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>CN(C)C=O>[NH2:2][C@@H:3]1[C:9](=[O:10])[N:8]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[S:5][C@H:4]1[C:15]1[S:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 67931170HCID 67931170, compound

Product 1

HCID 67931189HCID 67931189, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

With 100 ml of dimethylformamide is mixed 12.2 g of trans-3-amino-2-(2-thienyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrobromide, and 2.7 g of 60% sodium hydride is added to the mixture under ice-cooling. The reaction temperature is gradually elevated to room temperature. The mixture is stirred for 2 hours. After the reaction mixture is cooled again to about 10° C., 5.7 g of ethyl bromoacetate is added dropwise. The reaction temperature is elevated to room temperature, and thereafter the mixture is stirred for one night and concentrated under reduced pressure. Ice water and ethyl acetate are poured to the residue to extract the organic substance. The ethyl acetate layer is washed with water, and dried. After the solvent is distilled off under reduced pressure, the obtained residue is purified by silica gel chromatography to give 8.0 g of ethyl trans-3-amino-4-oxo-2-(2-thienyl)-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate as oily substance.

Workup

  1. additionis added to the mixture under ice-
  2. temperaturecooling
  3. customis gradually elevated to room temperature
  4. customis elevated to room temperature
  5. stirringthe mixture is stirred for one night
  6. concentrationconcentrated under reduced pressure
  7. additionIce water and ethyl acetate are poured to the residue
  8. extractionto extract the organic substance
  9. washThe ethyl acetate layer is washed with water
  10. customdried
  11. distillationAfter the solvent is distilled off under reduced pressure
  12. customthe obtained residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-98f20f6674d34367876517b4f6aa6d0e
Source dataset
uspto-grants-1991_10
Patent number
US05055464

Reaction notes

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