Ethyl bromoacetate → HCID 14648629, compound

HRID 345147Notes

Reaction equation

HRID 345147 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH:15]([NH:16][C:17]([C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=3)=[O:18])[C:14](=[O:29])[NH:13][C:12]3[CH:30]=[CH:31][CH:32]=[CH:33][C:11]=3[S:10]2)=[CH:5][CH:4]=1.[H-].[Na+].Br[CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH:15]([NH:16][C:17]([C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=3)=[O:18])[C:14](=[O:29])[N:13]([CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[C:12]3[CH:30]=[CH:31][CH:32]=[CH:33][C:11]=3[S:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 14648628HCID 14648628, compound

Product 1

HCID 14648629HCID 14648629, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In the same manner as in (iv) of Example 1, 1.5 g of 2-p-methoxyphenyl-3-(2-naphthalenecarboxamido)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one is dissolved in 30 ml of dimethylformamide, whereto 0.145 g of 60% sodium hydride is added under ice-cooling. After the mixture is stirred at room temperature for 30 minutes, 5 ml of dimethylformamide containing 0.45 ml of ethyl bromoacetate is added dropwise. The mixture is stirred at room temperature for 3 hours, and then the reaction mixture is concentrated under reduced pressure. Chloroform and water are added to the residue to separate the organic layer. The chloroform layer is washed with water and dried. The solvent is distilled off under reduced pressure. A mixed solvent of isopropyl alcohol-isopropyl ether is added thereto. The resulting crystals are collected by filtration to give 1.8 g of ethyl 2-p-methoxyphenyl-3-(2-naphthalenecarboxamido)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5acetate, m.p. 183°-186° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture is stirred at room temperature for 3 hours
  3. concentrationthe reaction mixture is concentrated under reduced pressure
  4. additionChloroform and water are added to the residue
  5. customto separate the organic layer
  6. washThe chloroform layer is washed with water
  7. customdried
  8. distillationThe solvent is distilled off under reduced pressure
  9. additionA mixed solvent of isopropyl alcohol-isopropyl ether is added
  10. filtrationThe resulting crystals are collected by filtration

Sources & evidence

ORD record
ord-1cd8886fac05485ab306fa8d8c62fb12
Source dataset
uspto-grants-1991_10
Patent number
US05055464

Reaction notes

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