Trifluoroacetic acid → HCID 15660486, compound

HRID 1196090Notes

Reaction equation

HRID 1196090 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:32]=[CH:33][C:34]=1[O:35][C:36](=[O:38])[CH3:37])[C:8]([O:10][CH2:11][C:12]1[CH2:19][S:18][CH:17]2[N:14]([C:15](=[O:28])[CH:16]2[NH:20]C(OC(C)(C)C)=O)[C:13]=1[C:29]([OH:31])=[O:30])=[O:9])(=[O:3])[CH3:2].C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:32]=[CH:33][C:34]=1[O:35][C:36](=[O:38])[CH3:37])[C:8]([O:10][CH2:11][C:12]1[CH2:19][S:18][C@H:17]2[N:14]([C:15](=[O:28])[C@H:16]2[NH2:20])[C:13]=1[C:29]([OH:31])=[O:30])=[O:9])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 85445614HCID 85445614, compound

Product 1

HCID 15660486HCID 15660486, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a magnetically stirred 500 mL flask under argon at room temperature (about 23° C.) was added 25.69 g of (6R-trans)-3-[[[3,4-bis(acetyloxy)-benzoyl]oxy]methyl-7-[[1,1dimethylethoxycarbonyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid and 250 mL of methylene chloride. This was followed by the addition of 25 mL of anisole and 250 mL of trifluoroacetic acid. Stirring was continued for 3 hours and then the solvents removed in vacuo. To the oil residue was added 200 mL of ethyl acetate and stirred for 20 minutes causing precipitation. 650 mL of anhydrous ether was added to this suspension and stirred for 10 minutes. The mixture was filtered on a Buchner funnel and dried under high vacuum to give 20.25 g (76.9%) of the named product.

Workup

  1. customthe solvents removed in vacuo
  2. additionTo the oil residue was added 200 mL of ethyl acetate
  3. stirringstirred for 20 minutes
  4. customprecipitation
  5. addition650 mL of anhydrous ether was added to this suspension
  6. stirringstirred for 10 minutes
  7. filtrationThe mixture was filtered on a Buchner funnel
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-0b7d800b37a84e12ae598e48693650e6
Source dataset
uspto-grants-1992_05
Patent number
US05112967

Reaction notes

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