Methyl triflate → HCID 178462288, compound

HRID 382640Notes

Reaction equation

HRID 382640 reaction equation
[CH:1]([C:3]1[N:10]2[C:6]([S:7][C:8]([C:11]3[C@H:12]([CH3:35])[C@@H:13]4[C@@H:30]([C@H:31]([OH:33])[CH3:32])[C:29](=[O:34])[N:14]4[C:15]=3[C:16]([O:18]CC3C=CC([N+]([O-])=O)=CC=3)=[O:17])=[CH:9]2)=[CH:5][N:4]=1)=[O:2].F[C:37](F)(F)S(OC)(=O)=O>ClCCl>[CH:1]([C:3]1[N:4]([CH3:37])[CH:5]=[C:6]2[N+:10]=1[CH:9]=[C:8]([C:11]1[C@H:12]([CH3:35])[C@@H:13]3[C@@H:30]([C@H:31]([OH:33])[CH3:32])[C:29](=[O:34])[N:14]3[C:15]=1[C:16]([O-:18])=[O:17])[S:7]2)=[O:2]

Participants

4

Reactant 2

HCID 9526Methyl triflateHCID 131722912HCID 131722912, compound

Product 1

HCID 178462288HCID 178462288, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 33 mg of 4-nitrobenzyl (1S,5R,6S)-2-(5-formylimidazo[5,1-b]thiazol-2-yl)-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate in 1 ml of dichloromethane was added 0.017 ml of methyl trifluoromethanesulfonate under ice-cooling. The mixture was stirred for 5 hours, and concentrated under reduced pressure. The residual concentrate was dissolved in 2 ml of THF and 2 ml of 1/15 M sodium phosphate buffer (pH 6.6), and 47 mg of 10% Pd-C was added therto. The reactor was purged with hydrogen, and the reaction mixture was stirred at room temperature for 2 hours. The catalyst was collected by filtration on Celite, and washed with water. The filtrate was washed with ethyl acetate, and the aqueous layer was purified by column chromatography on DIAION HP-20 (20% methanol in water) and on COSMOSEAL 40C18-PREP (water:methanol=10:1) to give 2.5 mg of the title compound.

Workup

  1. temperaturecooling
  2. concentrationconcentrated under reduced pressure
  3. concentrationThe residual concentrate
  4. dissolutionwas dissolved in 2 ml of THF
  5. addition2 ml of 1/15 M sodium phosphate buffer (pH 6.6), and 47 mg of 10% Pd-C was added
  6. customThe reactor was purged with hydrogen
  7. stirringthe reaction mixture was stirred at room temperature for 2 hours
  8. filtrationThe catalyst was collected by filtration on Celite
  9. washwashed with water
  10. washThe filtrate was washed with ethyl acetate
  11. customthe aqueous layer was purified by column chromatography on DIAION HP-20 (20% methanol in water) and on COSMOSEAL 40C18-PREP (water:methanol=10:1)

Sources & evidence

ORD record
ord-d7c8be39768c4bb0b9686b38a7304d60
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

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