Ethyl bromoacetate → [(4-t-Butoxycarbonylamino-butyl)-propyl-amino]-acetic acid ethyl ester

HRID 2080874Notes

Reaction equation

HRID 2080874 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][CH2:14][CH3:15])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>C(Cl)(Cl)Cl>[CH2:29]([O:28][C:26](=[O:27])[CH2:25][N:12]([CH2:11][CH2:10][CH2:9][CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:16])[CH2:13][CH2:14][CH3:15])[CH3:30]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 86071285(4-Propylamino-butyl)-carbamic acid t-butyl ester

Product 1

HCID 86614915[(4-t-Butoxycarbonylamino-butyl)-propyl-amino]-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The compound (339.0 mg) obtained in Example 84-1 was dissolved in chloroform (5.1 ml) and added with triethylamine (0.41 ml). Ethyl bromoacetate (0.20 ml) was dropped to the solution and the whole was stirred at room temperature for 2 days. After completion of the reaction, the solvent was distilled off. The residue was dissolved in chloroform and washed with a 1 mol/l sodium hydroxide aqueous solution, followed by extraction with chloroform. The organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off. The residue was purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (273.9 mg) as a colorless oily substance.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. dissolutionThe residue was dissolved in chloroform
  4. washwashed with a 1 mol/l sodium hydroxide aqueous solution
  5. extractionfollowed by extraction with chloroform
  6. washThe organic layer was washed with a saturated saline solution
  7. dry with materialdried with anhydrous sodium sulfate
  8. filtrationAfter filtration
  9. distillationthe solvent was distilled off
  10. customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9c38f85586ec4adaa4aa19c5d7b39ffb
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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