Triethylamine → HCID 19420321, compound

HRID 863768Notes

Reaction equation

HRID 863768 reaction equation
[Br:1][CH2:2][CH:3]([OH:7])[CH2:4][CH2:5][Br:6].C(O[CH:12]1[NH:15][C:14](=[O:16])[CH2:13]1)(=O)C.C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC=CC=1>[Br:1][CH2:2][CH:3]([O:7][CH:12]1[NH:15][C:14](=[O:16])[CH2:13]1)[CH2:4][CH2:5][Br:6]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 295701,4-Dibromo-2-butanolHCID 1199814-Acetoxy-2-azetidinone

Product 1

HCID 19420321HCID 19420321, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 1,4-dibromo-2-butanol (5.8 ml), 4-Acetoxyazetidinone (6.46 g), Palladium acetate (450 mg), Triethylamine (7 ml) and dry Benzene (75 ml) was stirred at room temperature under nitrogen for 23 hrs. Resulting solid was filtered off and filtrate was washed with water, brine and then dried over Magnesium sulfate. The residual oil, after evaporation, was purified by column chromatography using Hexane and Ethyl acetate (2:1) and the title compound was obtained. Yield: 5.88 g (78%). NMR (CDCl3): 2.05-2.17 (2H, m), 2.87-3.27 (2H, m), 3.42-3.60 (4H, m), 3.90-4.02 (1H, m), 5.23-5.33 (1H, m), 6.53 (1H, br, s). IR (Neat), cm-1 : 3260, 1771.

Workup

  1. customResulting solid
  2. filtrationwas filtered off
  3. washfiltrate was washed with water, brine
  4. dry with materialdried over Magnesium sulfate
  5. customThe residual oil, after evaporation
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-ff00a70806a14de29c5e656dc5205010
Source dataset
uspto-grants-1996_10
Patent number
US05561126

Reaction notes

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