Ethyl bromoacetate → HCID 69654916, compound

HRID 1244051Notes

Reaction equation

HRID 1244051 reaction equation
C1(S([CH2:10][C:11]2[C:12]([N+:24]([O-:26])=[O:25])=[N:13][C:14]([CH:19]3[O:23][CH2:22][CH2:21][O:20]3)=[C:15]([O:17][CH3:18])[CH:16]=2)(=O)=O)C=CC=CC=1.Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].CC(C)([O-])C.[K+]>C(O)C>[CH2:32]([O:31][C:29](=[O:30])[CH:28]=[CH:10][C:11]1[C:12]([N+:24]([O-:26])=[O:25])=[N:13][C:14]([CH:19]2[O:20][CH2:21][CH2:22][O:23]2)=[C:15]([O:17][CH3:18])[CH:16]=1)[CH3:33]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 21931738HCID 21931738, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 69654916HCID 69654916, compoundYield 126.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.28 g (0.73 mmol) 3-benzenesulfonylmethyl-6-[1,3]dioxolan-2-yl-5-methoxy-2-nitro-pyridine and 0.8 ml (0.73 mmol) of ethyl bromoacetate was dissolved in 10 ml of ethanol. To this solution was added 0.5 ml of potassium t-butoxide (1M in t-butyl alcohol) and the reaction mixture was stirred at room temperature for 1 hour. The solvent was evaporated and the residue was added to 5 ml of water. The suspension was extracted with ethyl acetate. The ethyl acetate extract was dried (Na2SO4) and evaporated to yield approximately 0.3 g of an oil. Mass spectrum: m/e=325.1 (p+1). This material was used directly in step 6.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was added to 5 ml of water
  3. extractionThe suspension was extracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. dry with materialwas dried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-a8725e3c7a07468183cb7c4f45eb4126
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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