Chloroform → HCID 54261344, compound

HRID 1706521Notes

Reaction equation

HRID 1706521 reaction equation
C(Cl)(Cl)Cl.[CH3:5][O:6][C:7]([CH:9]([N:17]1[CH2:20][CH:19]([NH:21][C:22](=[O:30])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]1=[O:31])[C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)=[O:8].[Br:32]Br.C(OCC)(=O)C>O1CCOCC1>[CH3:5][O:6][C:7]([CH:9]([N:17]1[CH2:20][CH:19]([NH:21][C:22](=[O:30])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]1=[O:31])[C:10]1[CH:11]=[CH:12][C:13]([OH:16])=[C:14]([Br:32])[CH:15]=1)=[O:8]

Participants

6

Reactant 4

HCID 6212Chloroform2×HCID 8857Ethyl AcetateHCID 24408BromineHCID 54381947HCID 54381947, compound

Product 1

HCID 54261344HCID 54261344, compoundYield 8.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Chloroform (1.5 ml.) was added to a solution of 1-(α-methoxycarbonyl-4-hydroxybenzyl)-3-(2-phenylacetamido)-2-azetidinone (184 mg.) dissolved in dioxane (2 ml.), and a chloroform (0.5 ml.) solution containing bromine (184 mg.) was added dropwise to said mixture in 5 minutes under ice-cooling. After addition of ethyl acetate (80 ml.) to said reaction mixture, the ethyl acetate layer was separated out, washed with water and dried over anhydrous magnesium sulfate. This solution was concentrated, and the residue was dissolved in a small amount of acetone. The solution was subjected to preparative thin layer chromatography using silica.gel [developing solvent; a mixture of chloroform and methanol (5:0.3)] for isolation and purification. The product thus obtained was recrystallized from a mixture of ethyl acetate and acetone to give 1-(α-methoxycarbonyl-3-bromo-4-hydroxybenzyl)-3-(2-phenylacetamido)-2-azetidinone (18 mg.). Mp 151° to 153° C. (dec.).

Workup

  1. additionwas added dropwise
  2. customin 5 minutes
  3. temperaturecooling
  4. customreaction mixture
  5. customthe ethyl acetate layer was separated out
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationThis solution was concentrated
  9. dissolutionthe residue was dissolved in a small amount of acetone
  10. additiona mixture of chloroform and methanol (5:0.3)]
  11. customfor isolation and purification
  12. customThe product thus obtained
  13. customwas recrystallized from a mixture of ethyl acetate and acetone

Sources & evidence

ORD record
ord-2b310fa5e3bd492f8908f528f249fba3
Source dataset
uspto-grants-1980_06
Patent number
US04207234

Reaction notes

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