Ethyl bromoacetate → HCID 13338732, compound

HRID 485670Notes

Reaction equation

HRID 485670 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×

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

Sources & evidence

ORD record
ord-da8be1d2d8214dbd9b0ed27eb1c3bc49
Source dataset
uspto-grants-1985_08
Patent number
US04537885

Reaction notes

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