Ethyl bromoacetate → HCID 20077201, compound

HRID 1654955Notes

Reaction equation

HRID 1654955 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>[CH2:31]([O:30][C:28](=[O:29])[CH2:27][O:19][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[CH2:11][CH:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:18]2)[CH3:32]

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

1.85 g (6.20 mmol) of 2-(t-butoxycarbonylaminomethyl)5-hydroxyindan was dissolved in 20 ml of acetone, to which were added 1.52 g (11.0 mmol) of potassium carbonate and 1.10 g (6.60 mmol) of ethyl bromoacetate, and refluxed for 3.5 hours. After cooling, the precipitates were filtrated, and the residue obtained by condensing the filtrate was purified by silica gel column chromatography (ethyl acetate:hexane=1:2) to obtain 1.90 g of colorless crystals. Yield: 80%

Workup

  1. temperaturerefluxed for 3.5 hours
  2. temperatureAfter cooling
  3. filtrationthe precipitates were filtrated
  4. customthe residue obtained by condensing the filtrate
  5. customwas purified by silica gel column chromatography (ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-e69685a5711641a9bd81678d56ad4eb4
Source dataset
uspto-grants-1995_04
Patent number
US05409956

Reaction notes

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