tert-Butyl bromoacetate → HCID 14182511, compound

HRID 1252624Notes

Reaction equation

HRID 1252624 reaction equation
[C:1]1([CH2:7][O:8][C:9]([NH:11][NH2:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].C(N(CC)C(C)C)(C)C>CN(C)C=O>[C:1]1([CH2:7][O:8][C:9]([NH:11][NH:12][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 79177tert-Butyl bromoacetateHCID 79242Benzyl carbazateHCID 81531Diisopropylethylamine

Product 1

HCID 14182511HCID 14182511, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Into a stirred solution of 6.65 g (0.040 mol) of N-[(phenylmethoxy)carbonyl]hydrazine in 40 ml of dimethylformamide was dropped a solution of 8.58 g (0.044 mol) of t-butyl bromoacetate in 20 ml of dimethylformamide followed by a solution of 8.2 ml (0.048 mol) of N,N-diisopropylethylamine in 8 ml of dimethylformamide. After the mixture had been stirred at room temperature for one day, the solvent was distilled off in vacuo and the residue was taken up in ether and water. The organic layer was washed three times with water, dried (magnesium sulfate) and evaporated in vacuo to leave an oil (10.6 g), which was purified by column chromatography on silica gel eluting with ethyl acetate/toluene (1:1). The appropriate fractions were evaporated in vacuo and the residue was stirred with petroleum ether yielding 6.0 g of the title compound, melting point 61°-62° C.

Workup

  1. distillationthe solvent was distilled off in vacuo
  2. washThe organic layer was washed three times with water
  3. dry with materialdried (magnesium sulfate)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-bb7f077972ee4cd9a5a79c26bfa330dd
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

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