Ethyl bromoacetate → HCID 13338732, compound

HRID 2417848Notes

Reaction equation

HRID 2417848 reaction equation
[N:1]([CH:4]1[CH2:12][CH2:11][CH2:10][CH2:9][C:8]2[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=2[NH:6][C:5]1=[O:17])=[N+:2]=[N-:3].CC(C)([O-])C.[K+].Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>CN(C)C=O>[N:1]([CH:4]1[CH2:12][CH2:11][CH2:10][CH2:9][C:8]2[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=2[N:6]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:5]1=[O:17])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 13338731HCID 13338731, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 13338732HCID 13338732, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 3-azido-1,3,4,5,6,7-hexahydro-1-benzazonin-2-one (8.9 g) in dry dimethylformamide (100 ml) is added during 30 minutes to a solution of potassium t-butoxide (4.5 g) in dry dimethylformamide (100 ml) maintained at 0° C. under an atmosphere of dry nitrogen. The reaction mixture is stirred at 0° C. for 2 hours, when a solution of ethyl bromoacetate (5.8 g) in dimethylformamide (10 ml) is added during 5 minutes. The reaction mixture is stirred at 0° C. for 2 hours, then evaporated under reduced pressure. The residue is distributed between ethyl acetate (250 ml) and water (150 ml), and the ethyl acetate solution washed with water (100 ml) and dried over sodium sulfate. The solvent is removed under reduced pressure to give 3-azido-1-ethoxycarbonylmethyl-1,3,4,5,6,7-hexahydro-1-benzazonin-2-one.

Workup

  1. stirringThe reaction mixture is stirred at 0° C. for 2 hours
  2. customevaporated under reduced pressure
  3. washthe ethyl acetate solution washed with water (100 ml)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-d045e400cc6048cdb9bbd1650da71396
Source dataset
uspto-grants-1984_09
Patent number
US04470988

Reaction notes

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