Iodomethyl pivalate → Pivaloyloxymethyl (1S,5R,6S)-2-(7-acetylimidazo[5,1-b]thiazol-2-yl)-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate

HRID 382652Notes

Reaction equation

HRID 382652 reaction equation
[C:1]([C:4]1[N:5]=[CH:6][N:7]2[CH:11]=[C:10]([C:12]3[C@H:13]([CH3:26])[C@@H:14]4[C@@H:21]([C@H:22]([OH:24])[CH3:23])[C:20](=[O:25])[N:15]4[C:16]=3[C:17]([O-:19])=[O:18])[S:9][C:8]=12)(=[O:3])[CH3:2].[Na+].[C:28]([O:34][CH2:35]I)(=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30]>CN(C=O)C.C(OCC)(=O)C>[C:1]([C:4]1[N:5]=[CH:6][N:7]2[CH:11]=[C:10]([C:12]3[C@H:13]([CH3:26])[C@@H:14]4[C@@H:21]([C@H:22]([OH:24])[CH3:23])[C:20](=[O:25])[N:15]4[C:16]=3[C:17]([O:19][CH2:35][O:34][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[O:18])[S:9][C:8]=12)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 104401Iodomethyl pivalateHCID 23698608Sodium (1s,5r,6s)-2-(7-acetylimidazo[5,1-b]thiazol-2-yl)-6-((1r)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate

Product 1

HCID 131722931Pivaloyloxymethyl (1S,5R,6S)-2-(7-acetylimidazo[5,1-b]thiazol-2-yl)-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 38.1 mg of sodium (1S,5R,6S)-2-(7-acetylimidazo[5,1-b]thiazol-2-yl)-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate in 3 ml of DMF was added 0.021 ml of pivaloyloxymethyl iodide under the atmosphere of argon at −30° C., and the mixture was stirred for 1.5 hours. The reaction mixture was diluted with 20 ml of ethyl acetate and washed with 20 ml of semi-saturated aqueous saline. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to a volume of 3 ml. The residue thus obtained was purified by column chromatography on silica gel (dichloromethane:methanol=20:1) and on Sephadex LH-20 (chloroform:methanol=1:1) in this sequence to give 35.8 mg of the title compound.

Workup

  1. washwashed with 20 ml of semi-saturated aqueous saline
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure to a volume of 3 ml
  5. customThe residue thus obtained
  6. customwas purified by column chromatography on silica gel (dichloromethane:methanol=20:1) and on Sephadex

Sources & evidence

ORD record
ord-149513e783a84f4e9172a8bb7c728042
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

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