Dimethylformamide → HCID 131718111, compound

HRID 5063Notes

Reaction equation

HRID 5063 reaction equation
[CH3:1][C:2]1[O:6][C:5](=[O:7])[O:4][C:3]=1[CH2:8]I.[O:10]=[C:11]1[CH:15]([S:16][C:17]2[C@H:18]([CH3:31])[C@@H:19]3[C@@H:26]([C@H:27]([OH:29])[CH3:28])[C:25](=[O:30])[N:20]3[C:21]=2[C:22]([O-:24])=[O:23])[CH2:14][CH2:13][NH:12]1.[Na+].CN(C)C=O>C(Cl)(Cl)Cl.C(OCC)(=O)C>[O:10]=[C:11]1[CH:15]([S:16][C:17]2[C@H:18]([CH3:31])[C@@H:19]3[C@@H:26]([C@H:27]([OH:29])[CH3:28])[C:25](=[O:30])[N:20]3[C:21]=2[C:22]([O:24][CH2:8][C:3]2[O:4][C:5](=[O:7])[O:6][C:2]=2[CH3:1])=[O:23])[CH2:14][CH2:13][NH:12]1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 189421374-(Iodomethyl)-5-methyl-2H-1,3-dioxol-2-oneHCID 131718112HCID 131718112, compound

Product 1

HCID 131718111HCID 131718111, compoundYield 45.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 66 mg of 5-methyl-2-oxo-1,3-dioxolen-4-ylmethyl iodide (prepared by heating 5-methyl-2-oxo-1,3-dioxolen-4-ylmethyl bromide and sodium iodide under reflux in acetone) in chloroform was added to a mixture of 47.6 mg of sodium (1R, 5S, 6S)-2-(2-oxo-3-pyrrolidinylthio)-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate and 0.4 ml of dry dimethylformamide. The mixture was stirred at room temperature for 80 minutes and then at 30°-45° C. for 4.5 hours. At the end of this time, the reaction mixture was diluted with ethyl acetate and washed four times with an aqueous solution of sodium chloride. The extract was dried and the solvent was distilled off under reduced pressure. The residue was purified by Lobar column chromatography (Merck, LiChroprep Si60, size A), eluted with a 10:1 by volume mixture of ethyl acetate and methanol, to give 27.4 mg of the title compound in the form of a colorless powder.

Workup

  1. waitat 30°-45° C. for 4.5 hours
  2. washwashed four times with an aqueous solution of sodium chloride
  3. customThe extract was dried
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by Lobar column chromatography (Merck, LiChroprep Si60, size A),
  6. washeluted with a 10:1 by volume mixture of ethyl acetate and methanol

Sources & evidence

ORD record
ord-d17197b3300b4c588249b50f58b34560
Source dataset
uspto-grants-1993_09
Patent number
US05242914

Reaction notes

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