Trifluoroacetic acid → HCID 131715083, compound

HRID 1906615Notes

Reaction equation

HRID 1906615 reaction equation
[Na+].C(OC([NH:9][C@H:10]1[C@@H:13](/[C:14](/[CH3:21])=[CH:15]\[C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:12]([S:22]([O-:25])(=[O:24])=[O:23])[C:11]1=[O:26])=O)(C)(C)C.FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1.CCOCC.CCCCCC>[NH2:9][C@H:10]1[C@@H:13](/[C:14](/[CH3:21])=[CH:15]\[C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:12]([S:22]([OH:25])(=[O:23])=[O:24])[C:11]1=[O:26]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131715084HCID 131715084, compound

Product 1

HCID 131715083HCID 131715083, compoundYield 66.3%

Reagents, catalysts & solvents 2

HCID 7519AnisoleSolventHCID 21584099Diethylether hexaneSolvent

Conditions

Temperature
-20 °C

Procedure

1.755 g (4.38 mmol) of rac-cis-3-(1-t-butoxyformamido)-4-[(Z)-2-(ethoxycarbonyl)-1-methylvinyl]-2-oxo-1-azetidinesulphonic acid sodium salt are dissolved in 7.5 ml of anisole and the solution is treated at -20° C. with 10 ml of trifluoroacetic acid. After stirring at -20° C. for 30 minutes and then at room temperature for a further 3 hours, the solution is diluted with 300 ml of ether/n-hexane (1:1). The crystals obtained are filtered off, dissolved in 10 ml of water and chromatographed on MCI gel. 808 mg (60%) of rac-cis-3-amino-4-[(Z)-2-(ethoxycarbonyl)-1-methylvinyl]-2-oxo-1-azetidinesulphonic acid are obtained.

Workup

  1. waitat room temperature for a further 3 hours
  2. customThe crystals obtained
  3. filtrationare filtered off
  4. dissolutiondissolved in 10 ml of water
  5. customchromatographed on MCI gel

Sources & evidence

ORD record
ord-c882b0dcf2574fd0b021606556279ce6
Source dataset
uspto-grants-1987_03
Patent number
US04652651

Reaction notes

Loading…