Ethyl bromoacetate → HCID 20077201, compound

HRID 1289448Notes

Reaction equation

HRID 1289448 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([OH:19])[CH:16]=2)[CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>CC(C)=O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:19][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:16]=2)[CH2:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 18921482HCID 18921482, compound

Product 1

HCID 20077201HCID 20077201, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Dissolved in 20 ml of acetone were 1.85 g (6.20 mmol) of 2-(t-butoxycarbonylaminomethyl)-5-hydroxyindane, and 1.52 g (11.0 mmol) of potassium carbonate and 1.10 g (6.60 mmol) of ethyl bromoacetate were added to the solution. The mixture was refluxed for 3.5 hours. After cooling, solids were separated by filtration, and the filtrate was concentrated. The resultant residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:2) to obtain 1.90 g of a colorless crystal. Yield; 80%.

Workup

  1. additionwere added to the solution
  2. temperatureThe mixture was refluxed for 3.5 hours
  3. temperatureAfter cooling
  4. customsolids were separated by filtration
  5. concentrationthe filtrate was concentrated
  6. customThe resultant residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-108e28cbbdbc4ceba5f4aa26b0905853
Source dataset
uspto-grants-1998_05
Patent number
US05750524

Reaction notes

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