Trifluoroacetic acid → HCID 70373604, compound

HRID 1709379Notes

Reaction equation

HRID 1709379 reaction equation
[Na+].C(OC([NH:9][C@@H:10]1[C@@H:13](/[CH:14]=[CH:15]/[C:16](=[O:18])[NH2:17])[N:12]([S:19]([O-:22])(=[O:21])=[O:20])[C:11]1=[O:23])=O)(C)(C)C.FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1.CCOCC.CCCCCC.O>[NH2:9][C@H:10]1[C@H:13](/[CH:14]=[CH:15]/[C:16](=[O:18])[NH2:17])[N:12]([S:19]([OH:22])(=[O:20])=[O:21])[C:11]1=[O:23]

Participants

7

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70373631HCID 70373631, compound

Product 1

HCID 70373604HCID 70373604, compoundYield 101.9%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 7519AnisoleSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

1.55 g (4.34 mmol) of (3R,4R)-3-(1-t-butoxyformamido)-4-[(E)-2-carbamoylvinyl]-2-oxo-1-azetidinesulphonic acid sodium salt are dissolved in 5 ml of anisole, the solution is cooled to 0° C. and then treated with 5 ml of trifluoroacetic acid. The suspension obtained is stirred at 0° C. for 1 hour and subsequently at room temperature for 2 hours. The mixture is diluted with 100 ml of ether and 20 ml of n-hexane. The crystals obtained are filtered off and dried. The thus-obtained crude material is dissolved in 10 ml of water and chromatographed on MCI gel using water for the elution. 1.04 g (100%) of (3S,4S)-3-amino-4-[(E)-2-carbamoylvinyl]-2-oxo-1-azetidinesulphonic acid are obtained.

Workup

  1. customThe suspension obtained
  2. customThe crystals obtained
  3. filtrationare filtered off
  4. customdried
  5. customThe thus-obtained crude material
  6. customchromatographed on MCI gel
  7. washfor the elution

Sources & evidence

ORD record
ord-db67b014da2044e6ad3670bddc0bfe2c
Source dataset
uspto-grants-1990_08
Patent number
US04948898

Reaction notes

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