Sodium hydride → Tert-butyl trans-3-amino-4-oxo-2-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate

HRID 345153Notes

Reaction equation

HRID 345153 reaction equation
[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][C:27]([CH3:30])([CH3:29])[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][C:27]([CH3:30])([CH3:29])[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

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 13490514trans-3-amino-2-phenyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

Product 1

HCID 13533191Tert-butyl trans-3-amino-4-oxo-2-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetateYield 94.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In 250 ml of dimethylformamide is dissolved 13.9 g of trans-3-amino-2-phenyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, and 2.3 g of 60% sodium hydride is added to the solution. After the mixture is stirred at room temperature for 20 minutes, 80 ml of a solution containing 10 g of tert-butyl bromoacetate in dimethylformamide is added thereto dropwise. The mixture is stirred at room temperature for 3 hours and then concentrated under reduced pressure. Water is added to the residue, and the organic substance is extracted with ethyl acetate. The ethyl acetate layer is washed with water and dried. Thereafter the solvent is distilled off under reduced pressure to give 18.6 g of tert-butyl trans-3-amino- 4-oxo-2-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate in the form of white crystals, m.p. 172°-174° C.

Workup

  1. additionis added to the solution
  2. additionis added
  3. stirringThe mixture is stirred at room temperature for 3 hours
  4. concentrationconcentrated under reduced pressure
  5. additionWater is added to the residue
  6. extractionthe organic substance is extracted with ethyl acetate
  7. washThe ethyl acetate layer is washed with water
  8. customdried
  9. distillationThereafter the solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-b164aefe71c64a1685a2c749a2fbd6c0
Source dataset
uspto-grants-1991_10
Patent number
US05055464

Reaction notes

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