Iodomethyl pivalate → HCID 131722932, compound

HRID 382653Notes

Reaction equation

HRID 382653 reaction equation
[CH3:1][N:2]([CH3:28])[C:3]([C:5]1[N:6]=[CH:7][N:8]2[CH:12]=[C:11]([C:13]3[C@@H:14]([CH3:27])[C@@H:15]4[C@@H:22]([C@H:23]([OH:25])[CH3:24])[C:21](=[O:26])[N:16]4[C:17]=3[C:18]([O-:20])=[O:19])[S:10][C:9]=12)=[O:4].[Na+].C(=O)([O-])O.[Na+].[C:35]([O:41][CH2:42]I)(=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37]>CN(C=O)C>[CH3:28][N:2]([CH3:1])[C:3]([C:5]1[N:6]=[CH:7][N:8]2[CH:12]=[C:11]([C:13]3[C@H:14]([CH3:27])[C@@H:15]4[C@@H:22]([C@H:23]([OH:25])[CH3:24])[C:21](=[O:26])[N:16]4[C:17]=3[C:18]([O:20][CH2:42][O:41][C:35](=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37])=[O:19])[S:10][C:9]=12)=[O:4]

Participants

5

Reactant 3

HCID 104401Iodomethyl pivalateHCID 516892Sodium BicarbonateHCID 131722933HCID 131722933, compound

Product 1

HCID 131722932HCID 131722932, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-30 °C

Procedure

To a solution of 50 mg of sodium (1R,5R,6S)-2-[7-(N,N-dimethylcarbamoyl)imidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-carbapen-2-em-3-carboxylate in 0.7 ml of DMF was added 5.0 mg of sodium hydrogen carbonate, and the mixture was cooled to −30° C. under the atmosphere of argon. The reaction mixture was added with 43 mg of pivaloyloxymethyl iodide, stirred for 1 hour, extracted with 20 ml of ethyl acetate, and the organic layer was washed with 12 ml of semi-saturated aqueous saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to a volume of about 1 ml. The residue thus obtained was purified by column chromatography on silica gel (dichloromethane:methanol=95:5) to give 55 mg of the title compound.

Workup

  1. extractionextracted with 20 ml of ethyl acetate
  2. washthe organic layer was washed with 12 ml of semi-saturated aqueous saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure to a volume of about 1 ml
  5. customThe residue thus obtained
  6. customwas purified by column chromatography on silica gel (dichloromethane:methanol=95:5)

Sources & evidence

ORD record
ord-79fe88aaf56145148f0996ef42b72c59
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

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