Ethyl bromoacetate → HCID 131727366, compound

HRID 1785475Notes

Reaction equation

HRID 1785475 reaction equation
[CH2:1]([NH:8][NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.Br[CH2:23][C:24]([O:26]CC)=[O:25]>CCCC[N+](CCCC)(CCCC)CCCC.[I-].CCN(CC)CC>[NH2:8][CH2:23][C:24]([OH:26])=[O:25].[CH2:1]([NH:8][NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetate2×HCID 8028TetrahydrofuranHCID 408153HCID 408153, compound

Product 1

HCID 131727366HCID 131727366, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8471TriethylamineSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of dibenzylhydrazine (5.30 g, 25.0 mmol) and THF (50 mL) and TBAI (0.46 g, 1.25 mmol) was added BrCH2CO2Et (2.64 mL, 23.8 mmol) and Et3N (3.32 mL, 23.8 mmol). The reaction mixture was stirred at 60° C. for 7 hours, an additional 0.3 eq. of base and electrophile were added (BrCH2CO2Et, 0.83 mL, 7.5 mmol and Et3N, 1.0 mL, 7.5 mmol). The reaction mixture was held overnight at R/T, an additional 0.3 eq. of each reagent was added and the reaction mixture was stirred at 60° C. for 4 more hours. The reaction mixture was partitioned with CH2Cl2, and the isolated organic fraction was washed with brine three (3 times), dried over Na2SO4, and concentrated in vacuo to afford 7.21 g, 24.2 mmol, (97%) of a crude oil.

Workup

  1. waitThe reaction mixture was held overnight at R/T
  2. stirringthe reaction mixture was stirred at 60° C. for 4 more hours
  3. customThe reaction mixture was partitioned with CH2Cl2
  4. washthe isolated organic fraction was washed with brine three (3 times)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ebeeb039964a4f5b90012c8ce5c1b9a9
Source dataset
uspto-grants-2009_03
Patent number
US07504521B2

Reaction notes

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