Ethyl bromoacetate → HCID 86609229, compound

HRID 2233739Notes

Reaction equation

HRID 2233739 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:11])=[C:5]2[O:12][C:13]1[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:6]([CH3:11])=[C:5]2[O:12][C:13]1[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetate2×HCID 11430Potassium Carbonate2×HCID 68616571HCID 68616571, compound

Product 1

HCID 86609229HCID 86609229, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the product from step (ii) (335 mg), potassium carbonate (0.3 g) and ethyl bromoacetate (0.16 ml) in DMF (5 ml) was stirred at RT. After 16 h, ethyl bromoacetate (0.1 ml) and potassium carbonate (0.15 g) were added and the mixture heated at 50° C. for 4 h then partitioned between diethylether/water. The organics were washed with water, dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 10% ethylacetate/iso-hexane. Yield 0.41 g

Workup

  1. temperaturethe mixture heated at 50° C. for 4 h
  2. customthen partitioned between diethylether/water
  3. washThe organics were washed with water
  4. customdried
  5. customevaporated under reduced pressure
  6. customThe residue was purified by chromatography on silica eluting with 10% ethylacetate/iso-hexane

Sources & evidence

ORD record
ord-c2b76d2948bd43878535d5fba86561cb
Source dataset
uspto-grants-2010_05
Patent number
US07709521B2

Reaction notes

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