Hydrochloric Acid → HCID 22105421, compound

HRID 1455884Notes

Reaction equation

HRID 1455884 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].C([O:12][C:13](=[O:27])[C:14](=[C:24]([CH3:26])[CH3:25])[N:15]1[C:18](=[O:19])[C:17]([Br:21])([Br:20])[CH:16]1[O:22][CH3:23])C1C=CC=CC=1.C1(OC)C=CC=CC=1.Cl>C(Cl)Cl.C(OCC)(=O)C>[Br:21][C:17]1([Br:20])[C:18](=[O:19])[N:15]([C:14](=[C:24]([CH3:26])[CH3:25])[C:13]([OH:27])=[O:12])[CH:16]1[O:22][CH3:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 54293415HCID 54293415, compound

Product 1

HCID 22105421HCID 22105421, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To an ice-cooled suspension of aluminum trichloride (0.400 g; 0.003 mole) in methylene chloride (15 mL) in a nitrogen stream a solution of 2-methoxy-3,3-dibromo-alpha-(1-methylethylidene)-4-oxo-1-azetidine acetic acid benzyl ester (0.447 g; 0.001 mole) and anisole (0.648 g; 0.65 mL, 0.006 mole) in methylene chloride (15 mL) was added and then it was stirred for half an hour at room temperature. Ethyl acetate (15 mL) and 0.1N hydrochloric acid (5 mL) were added to the reaction mixture and the layers were separated. The ethyl acetate layer was extracted with a 5% sodium hydrogen carbonate solution (2×20 mL) and the layers were separated. The aqueous layer was acidified with 0.1N hydrochloric acid to pH 1, then fresh ethyl acetate (20 mL) and sodium chloride were added and the layers were again separated. The ethyl acetate layer was washed with a saturated salt solution, dried and evaporated to a dry residue to obtain 3,3-dibromo-2-methoxy-alpha-(1-methylethylidene)-4-oxo-1-azetidine acetic acid, which was identical to the one disclosed under 2a.

Workup

  1. additionwas added
  2. customthe layers were separated
  3. extractionThe ethyl acetate layer was extracted with a 5% sodium hydrogen carbonate solution (2×20 mL)
  4. customthe layers were separated
  5. additionfresh ethyl acetate (20 mL) and sodium chloride were added
  6. customthe layers were again separated
  7. washThe ethyl acetate layer was washed with a saturated salt solution
  8. customdried
  9. customevaporated to a dry residue

Sources & evidence

ORD record
ord-f48a411754e244feb239ddcc35550ac7
Source dataset
uspto-grants-1998_12
Patent number
US05843939

Reaction notes

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