Methyl iodide → HCID 12070023, compound

HRID 382633Notes

Reaction equation

HRID 382633 reaction equation
[CH:1]([NH:3][CH2:4][C:5]1[N:6]=[CH:7][N:8]2[CH:12]=[C:11]([C:13]3[C@H:14]([CH3:37])[C@@H:15]4[C@@H:32]([C@H:33]([OH:35])[CH3:34])[C:31](=[O:36])[N:16]4[C:17]=3[C:18]([O:20]CC3C=CC([N+]([O-])=O)=CC=3)=[O:19])[S:10][C:9]=12)=[O:2].[CH3:38]I>CN(C=O)C.C1COCC1.P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+].[Pd]>[CH:1]([NH:3][CH2:4][C:5]1[N:6]([CH3:38])[CH:7]=[N+:8]2[CH:12]=[C:11]([C:13]3[C@H:14]([CH3:37])[C@@H:15]4[C@@H:32]([C@H:33]([OH:35])[CH3:34])[C:31](=[O:36])[N:16]4[C:17]=3[C:18]([O-:20])=[O:19])[S:10][C:9]=12)=[O:2]

Participants

7

Reactant 2

HCID 6328Methyl iodideHCID 88263412HCID 88263412, compound

Product 1

HCID 12070023HCID 12070023, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 24243Trisodium PhosphateSolvent

Procedure

To a solution of 134 mg of 4-nitrobenzyl (1S,5R,6S)-2-(7-formylaminomethyl imidazo[5,1-b]thiazol-2-yl)-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate in 2 ml of DMF was added 1.6 ml of methyl iodide, and the mixture was stirred at room temperature for 12 hours. The solvent was removed under reduced pressure. The residue thus obtained was dissolved in 5 ml of THF and 5 ml of 0.1 M sodium phosphate buffer (pH 6.8), and 150 mg of 10% Pd-C. The reactor was purged with hydrogen, the reaction mixture was stirred at room temperature for 1 hour. The catalyst was collected by filtration, and washed with a mixed solution of 2 ml of 0.1 M sodium phosphate buffer (pH 6.8) and 2 ml of THF. The filtrate was washed with 10 ml of ethyl acetate, and the aqueous layer obtained was purified by column chromatography on COSMOSEAL 40C18-PREP (water:methanol=20:1). The fraction containing the aimed product was concentrated under reduced pressure, and then lyophilized to give 58 mg of the title compound.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue thus obtained
  3. customThe reactor was purged with hydrogen
  4. stirringthe reaction mixture was stirred at room temperature for 1 hour
  5. filtrationThe catalyst was collected by filtration
  6. washwashed with a mixed solution of 2 ml of 0.1 M sodium phosphate buffer (pH 6.8) and 2 ml of THF
  7. washThe filtrate was washed with 10 ml of ethyl acetate
  8. customthe aqueous layer obtained
  9. customwas purified by column chromatography on COSMOSEAL 40C18-PREP (water:methanol=20:1)
  10. additionThe fraction containing the aimed product
  11. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-866dc54a4ca148eab7d9315de5b01e9f
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

Loading…