Methyl fluorosulfate → HCID 88417840, compound

HRID 1033672Notes

Reaction equation

HRID 1033672 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:52](=[O:53])[N:6]2[C:7]([C:39]([O:41]CC3C=CC([N+]([O-])=O)=CC=3)=[O:40])=[C:8]([S:11][C@@H:12]3[CH2:16][N:15](C(OCC4C=CC([N+]([O-])=O)=CC=4)=O)[C@H:14]([C:30](=[O:38])[NH:31][CH2:32][CH2:33][N+:34]([CH3:37])([CH3:36])[CH3:35])[CH2:13]3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].[F:54][S:55]([O:58]C)(=[O:57])=[O:56]>C(Cl)Cl>[F:54][S:55]([O-:58])(=[O:57])=[O:56].[OH:1][C@@H:2]([C@H:4]1[C:52](=[O:53])[N:6]2[C:7]([C:39]([OH:41])=[O:40])=[C:8]([S:11][C@@H:12]3[CH2:16][NH:15][C@H:14]([C:30](=[O:38])[NH:31][CH2:32][CH2:33][N+:34]([CH3:37])([CH3:35])[CH3:36])[CH2:13]3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

Participants

4

Reactant 2

HCID 9870Methyl fluorosulfateHCID 57253261HCID 57253261, compound

Product 1

HCID 88417840HCID 88417840, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

90 mg of 4-nitrobenzyl (1R,5S,6S)-6-[(1R)-1-hydroxyethyl]-1-methyl-2-[(2S,4S)-2-(2-trimethylammonioethylcarbamoyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio]-1-carbapen-2-em-3-carboxylate [prepared as described in step (2) above] were dissolved in 2 ml of anhydrous methylene chloride, and the solution was placed on an ice bath. Whilst the solution was still on the ice bath, 20 μl of methyl fluorosulfonate were added, and the resulting mixture was stirred for 30 minutes at room temperature. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting crude product was dissolved in 5 ml of a 1:1 by volume mixture of tetrahydrofuran and water. Hydrogen was passed through the resulting solution for 2 hours at room temperature in the presence of 90 mg of a 10% w/w palladium-on-carbon catalyst. At the end of this time, the catalyst was removed by filtration. The filtrate was condensed by evaporation under reduced pressure, and 5 ml of water were added to the residue. The soluble fraction was subjected to column chromatography through a Sephadex G-10 (Pharmacia, 40-120 μm) column, eluted with water. Those fractions containing the title compound were collected and lyophilized to give 53 mg of the title compound.

Workup

  1. customthe solution was placed on an ice bath
  2. additionwere added
  3. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  4. dissolutionthe resulting crude product was dissolved in 5 ml of a 1:1 by volume mixture of tetrahydrofuran and water
  5. waitHydrogen was passed through the resulting solution for 2 hours at room temperature in the presence of 90 mg of a 10% w/w palladium-on-carbon catalyst
  6. customAt the end of this time, the catalyst was removed by filtration
  7. customcondensed
  8. customby evaporation under reduced pressure, and 5 ml of water
  9. additionwere added to the residue
  10. wash(Pharmacia, 40-120 μm) column, eluted with water
  11. additionThose fractions containing the title compound
  12. customwere collected

Sources & evidence

ORD record
ord-bdeb4ac1d5ad4e76bb8eb3f058217de4
Source dataset
uspto-grants-1994_05
Patent number
US05310735

Reaction notes

Loading…