Iodomethyl pivalate → HCID 131722923, compound

HRID 382646Notes

Reaction equation

HRID 382646 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]([CH3:27])[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:2].[Na+].[C:29]([O:35][CH2:36]I)(=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31]>CN(C=O)C.ClCCl>[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]([CH3:27])[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][CH2:36][O:35][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])=[O:19])[S:10][C:9]=12)=[O:2]

Participants

5

Reactant 2

HCID 104401Iodomethyl pivalateHCID 131722924HCID 131722924, compound

Product 1

HCID 131722923HCID 131722923, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 33 mg of sodium (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 0.8 ml of DMF was added 29 mg of pivaloyloxymethyl iodide at −30° C., and the mixture was stirred for 1 hour during which the temperature was raised up to room temperature. The reaction mixture was diluted with 30 ml of dichloromethane, washed with semi-saturated aqueous saline, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue thus obtained was purified by column chromatography on silica gel (ethyl acetate:methanol=4:1) to give the title compound in a yield of 29 mg.

Workup

  1. washwashed with semi-saturated aqueous saline
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was removed under reduced pressure
  4. customthe residue thus obtained
  5. customwas purified by column chromatography on silica gel (ethyl acetate:methanol=4:1)

Sources & evidence

ORD record
ord-d6ccbcd7e4bf452ba972bdeec9115306
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

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