Hydrochloric Acid → HCID 14230833, compound

HRID 615110Notes

Reaction equation

HRID 615110 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:19](=[O:20])[N:18]2[CH:13]1[S:14][CH2:15][N:16]([S:31]([C:34]([F:37])([F:36])[F:35])(=[O:33])=[O:32])[CH:17]2[C:21]([O:23]CC1C=CC=CC=1)=[O:22])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(OC)C=CC=CC=1.C(OCC)(=O)C.Cl>C(Cl)Cl.[N+](C)([O-])=O>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:19](=[O:20])[N:18]2[CH:13]1[S:14][CH2:15][N:16]([S:31]([C:34]([F:35])([F:36])[F:37])(=[O:32])=[O:33])[CH:17]2[C:21]([OH:23])=[O:22])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 8857Ethyl AcetateHCID 14230826HCID 14230826, compound

Product 1

HCID 14230833HCID 14230833, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6375NitromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of benzyl 7-phenoxyacetamido-8-oxo-3-trifluoromethanesulfonyl-5-thia-1,3-diazabicyclo[4,2,0]octane-2-carboxylate (2.19 g.) and anisole (6.3 ml.) in methylene chloride (20 ml.) was added a solution of alminum trichloride (2.6 g.) in nitromethane (10 ml.) at 0° C. over a period of 5 minutes. The resultant deep red solution was stirred at 0° C. for 30 minutes. After the reaction mixture was poured into a mixture of ice and ethyl acetate (120 ml.), it was acidified to pH 1 with 3N hydrochloric acid. The organic layer was separated, washed twice with an aqueous solution of sodium chloride and hydrochloric acid and then extracted with a chilled dilute aqueous solution of sodium bicarbonate (once with 50 ml. and twice with 30 ml.). These aqueous extracts were combined, acidified to pH 1 with 3N hydrochloric acid, saturated with sodium chloride and then extracted three times with chloroform. Drying over magnesium sulfate and removal of the solvent afforded an amorphous solid (1.75 g.) of 7-phenoxyacetamido-8-oxo-3-trifluoromethanesulfonyl-5-thia-1,3-diazabicyclo[4,2,0]octane-2-carboxylic acid.

Workup

  1. customThe organic layer was separated
  2. washwashed twice with an aqueous solution of sodium chloride and hydrochloric acid
  3. extractionextracted with a chilled dilute aqueous solution of sodium bicarbonate (once with 50 ml
  4. extractionextracted three times with chloroform
  5. dry with materialDrying over magnesium sulfate and removal of the solvent

Sources & evidence

ORD record
ord-5e3947b5dfc347d1a6a5ae6328a71262
Source dataset
uspto-grants-1985_02
Patent number
US04497738

Reaction notes

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