Iodomethyl pivalate → HCID 131722913, compound

HRID 382641Notes

Reaction equation

HRID 382641 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:22](=[O:23])[N:6]2[C:7]([C:19]([O-:21])=[O:20])=[C:8]([C:11]3[N:12]=[CH:13][N:14]4[CH:18]=[CH:17][S:16][C:15]=34)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].[Na+].C(=O)([O-])O.[Na+].[C:30]([O:36][CH2:37]I)(=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32]>CN(C=O)C.C(OCC)(=O)C>[OH:1][C@@H:2]([C@H:4]1[C:22](=[O:23])[N:6]2[C:7]([C:19]([O:21][CH2:37][O:36][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])=[O:20])=[C:8]([C:11]3[N:12]=[CH:13][N:14]4[CH:18]=[CH:17][S:16][C:15]=34)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

Participants

6

Reactant 3

HCID 104401Iodomethyl pivalateHCID 516892Sodium BicarbonateHCID 131722914HCID 131722914, compound

Product 1

HCID 131722913HCID 131722913, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-30 °C

Procedure

To a solution of 27 mg of sodium (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-7-yl)-1-methyl-1-carbapen-2-em-3-carboxylate in 0.5 ml of DMF was added 4.0 mg of sodium hydrogen carbonate, and the mixture was cooled to −30° C. under the atmosphere of argon. Pivaloyloxymethyl iodide (30 mg) was added, and the reaction mixture was stirred at −20-−30° C. for 1 hour. The reaction mixture was diluted with 20 ml of ethyl acetate and 10 ml of semi-saturated aqueous saline, and the mixture was stirred and separated. The organic layer was washed with semi-saturated aqueous saline, dried over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure to a volume of about 1 ml. It was purified by column chromatography on silica gel (ethyl acetate-ethyl acetate:methanol=97:3), and the solvent was concentrated under reduced pressure to a volume of about 0.5 ml and added dropwise to isopropyl ether. The resulting precipitate was collected by filtration, and desiccated under reduced pressure to give 17 mg of the title compound.

Workup

  1. stirringthe mixture was stirred
  2. customseparated
  3. washThe organic layer was washed with semi-saturated aqueous saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationthe solvent was concentrated under reduced pressure to a volume of about 1 ml
  6. customIt was purified by column chromatography on silica gel (ethyl acetate-ethyl acetate:methanol=97:3)
  7. concentrationthe solvent was concentrated under reduced pressure to a volume of about 0.5 ml
  8. additionadded dropwise to isopropyl ether
  9. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-37a7bbac8a8047ad9f1d8d39d489ff55
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

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