Ethyl bromoacetate → HCID 14648536, compound

HRID 345144Notes

Reaction equation

HRID 345144 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[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[H-].[Na+].Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>CN(C)C=O>[NH2:2][C@H:3]1[C:9](=[O:10])[N:8]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[S:5][C@H:4]1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 68605990HCID 68605990, compound

Product 1

HCID 14648536HCID 14648536, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
10 °C

Procedure

With 40 ml of dimethylformamide is mixed 3 g of cis-3-amino-2-phenyl-2,3-dihydro-1,5-benzothiazepin-4(5H)- one hydrobromide in the same manner as in (iv) of Example 1, and 0.72 g of 60% sodium hydride is added to the mixture under ice-cooling. After the temperature is gradually elevated to room temperature, the mixture is stirred for 2 hours. After the temperature of the reaction mixture is again cooled to about 10° C., 5 ml of a dimethylformamide solution containing 1.1 ml of ethyl bromoacetate is added dropwise thereto. Then, the reaction temperature is elevated to room temperature, and the reaction mixture is stirred for 6 hours, followed by concentration under reduced pressure. By adding ice water and chloroform to the residue, the organic substance is extracted. The chloroform layer is washed with water and dried. Thereafter, the solvent is distilled off under reduced pressure. The purification of the obtained residue by silica gel chromatography gives 3.0 g of ethyl cis-3-amino-4-oxo-2-phenyl-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. additionis added dropwise
  5. customis elevated to room temperature
  6. stirringthe reaction mixture is stirred for 6 hours
  7. concentrationfollowed by concentration under reduced pressure
  8. additionBy adding ice water and chloroform to the residue
  9. extractionthe organic substance is extracted
  10. washThe chloroform layer is washed with water
  11. customdried
  12. distillationThereafter, the solvent is distilled off under reduced pressure
  13. customThe purification of the obtained residue by silica gel chromatography

Sources & evidence

ORD record
ord-42e92d0263e4484f8c0db2c19c99df88
Source dataset
uspto-grants-1991_10
Patent number
US05055464

Reaction notes

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