Ethyl bromoacetate → HCID 14856503, compound

HRID 1073331Notes

Reaction equation

HRID 1073331 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]([S:15]([NH2:18])(=[O:17])=[O:16])[C:4]=2[CH:3]=1.[H-].[Na+].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>CN(C)C=O.O>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][C:5]1([S:15]([NH2:18])(=[O:16])=[O:17])[C:4]2[CH:3]=[C:2]([Cl:1])[CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH3:27]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 14856502HCID 14856502, compound

Product 1

HCID 14856503HCID 14856503, compoundYield 59.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Under nitrogen, (21) (2.6 g, 9.3 mmoL) was added portionwise to a stirred suspension of sodium hydride (465 mg of a 60% mineral oil dispersion, 1.25 eq) in dry dimethylformamide (60 mL , from CaH2). After 30 minutes, ethyl bromoacetate (1.3 g, 11.6mmoL, 1.25 eq) was added and stirring was continued overnight. The reaction was then diluted with water (200 mL), neutralized, and extracted with ethyl acetate (3×200 mL). The combined organic phases were washed with brine (3×200 mL), dried (MgSO4), and concentrated. The crude solid was recrystallized twice from ethyl acetate/hexane to provide 1.7 g(50%) of product (22): mp 189°-191° C.

Workup

  1. waitwas continued overnight
  2. extractionextracted with ethyl acetate (3×200 mL)
  3. washThe combined organic phases were washed with brine (3×200 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude solid was recrystallized twice from ethyl acetate/hexane

Sources & evidence

ORD record
ord-069f313a896444b2af6760ed845d54db
Source dataset
uspto-grants-1990_11
Patent number
US04968809

Reaction notes

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