Ethyl bromoacetate → HCID 86609238, compound

HRID 2233759Notes

Reaction equation

HRID 2233759 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[N+:16]([O-:18])=[O:17])[NH:9][C:8]=2[CH3:19])=[CH:4][CH:3]=1.CC(C)([O-])C.[Na+].Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>C1COCC1>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[N+:16]([O-:18])=[O:17])[N:9]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:8]=2[CH3:19])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 23676156Sodium t-butoxideHCID 68616436HCID 68616436, compound

Product 1

HCID 86609238HCID 86609238, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from step (ii) (6.0 g) was dissolved in THF (100 ml), sodium t-butoxide (2.1 g) added, stirred for 10 min, ethyl bromoacetate (2.45 ml) added and stirred for a further 20 min. The reaction was quenched with 1M hydrochloric acid, extracted with EtOAc, washed with brine, dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on silica eluting with 20% ethylacetate/iso-hexane. Yield 6 g.

Workup

  1. stirringstirred for a further 20 min
  2. customThe reaction was quenched with 1M hydrochloric acid
  3. extractionextracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by chromatography on silica eluting with 20% ethylacetate/iso-hexane

Sources & evidence

ORD record
ord-078f84169451440e9ff10f73d0b46125
Source dataset
uspto-grants-2010_05
Patent number
US07709521B2

Reaction notes

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