Ethyl bromoacetate → HCID 11689289, compound

HRID 2233757Notes

Reaction equation

HRID 2233757 reaction equation
CC(C)([O-])C.[Na+].[CH3:7][C:8]1[NH:9][C:10]2[C:15]([C:16]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=1)=[CH:14][C:13]([CH3:28])=[CH:12][CH:11]=2.Br[CH2:30][C:31]([O:33]CC)=[O:32]>C1COCC1.O.[OH-].[Na+]>[CH3:7][C:8]1[N:9]([CH2:30][C:31]([OH:33])=[O:32])[C:10]2[C:15]([C:16]=1[O:17][C:18]1[CH:19]=[CH:20][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:22][CH:23]=1)=[CH:14][C:13]([CH3:28])=[CH:12][CH:11]=2

Participants

7

Reactant 3

HCID 7748Ethyl bromoacetateHCID 23676156Sodium t-butoxideHCID 68616142HCID 68616142, compound

Product 1

HCID 11689289HCID 11689289, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Sodium t-butoxide (220 mg) was added to a solution of the product from step (iii) (600 mg) in THF (20 ml) and stirred for 10 min. Ethyl bromoacetate (250 μl) was added and the reaction stirred for a further 1 h. The mixture was then diluted with water (10 ml), 1M aqueous sodium hydroxide (5 ml) added and stirred for 3 h. The mixture was extracted with EtOAc, washed with brine, dried (MgSO4), filtered and evaporated. The residue was purified using reverse phase preparative chromatography (eluent MeCN/NH3(aq)) to give the title compound. Yield 450 mg.

Workup

  1. stirringthe reaction stirred for a further 1 h
  2. additionadded
  3. stirringstirred for 3 h
  4. extractionThe mixture was extracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified

Sources & evidence

ORD record
ord-1065d01451974570a40427e3e25f96d0
Source dataset
uspto-grants-2010_05
Patent number
US07709521B2

Reaction notes

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