Iodomethyl pivalate → HCID 12069977, compound

HRID 382609Notes

Reaction equation

HRID 382609 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:22](=[O:23])[N:6]2[C:7]([C:19]([OH:21])=[O:20])=[C:8]([C:11]3[S:15][C:14]4=[CH:16][N:17]=[CH:18][N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].C(=O)([O-])O.[Na+].[C:29]([O:35][CH2:36]I)(=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31]>O.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][CH2:36][O:35][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])=[O:20])=[C:8]([C:11]3[S:15][C:14]4=[CH:16][N:17]=[CH:18][N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

Participants

7

Reactant 3

HCID 104401Iodomethyl pivalateHCID 516892Sodium BicarbonateHCID 9819016HCID 9819016, compound

Product 1

HCID 12069977HCID 12069977, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 947 mg of (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-2-yl)-1-methyl-1-carbapen-2-em-3-carboxylic acid in 180 ml of water was added 7.8 ml of 0.1 N aqueous sodium hydrogen carbonate, and the mixture was stirred at room temperature for 2 hours to form a solution, which was then frozen. The frozen solution was dissolved in 12 ml of dry DMF, mixed with 0.36 ml of iodomethyl pivalate under the atmosphere of argon at −30° C., and stirred for 1.5 hours during which the temperature was raised up to −10° C. The reaction mixture was diluted with 100 ml of ethyl acetate, and washed with 100 ml of semi-saturated aqueous saline. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to a total volume of 5 ml. The residue thus obtained was purified by column chromatography on silica gel (chloroform:methanol 10:1) and on Sephadex LH-20 (chloroform:methanol=1:1) in this sequence to give 576 mg of the title compound.

Workup

  1. customto form a solution, which
  2. temperaturewas then frozen
  3. stirringstirred for 1.5 hours during which the temperature
  4. temperaturewas raised up to −10° C
  5. washwashed with 100 ml of semi-saturated aqueous saline
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure to a total volume of 5 ml
  9. customThe residue thus obtained
  10. customwas purified by column chromatography on silica gel (chloroform:methanol 10:1) and on Sephadex

Sources & evidence

ORD record
ord-ba3b3c95091b49e19f37bd26ff156b00
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

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