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

HRID 382634Notes

Reaction equation

HRID 382634 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:18]4[C:14]([S:15][CH:16]=[CH:17]4)=[CH:13][N:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].[K+].[C:25]([O:31][CH2:32]I)(=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27]>CN(C=O)C.ClCCl>[OH:1][C@@H:2]([C@H:4]1[C:22](=[O:23])[N:6]2[C:7]([C:19]([O:21][CH2:32][O:31][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[O:20])=[C:8]([C:11]3[N:18]4[C:14]([S:15][CH:16]=[CH:17]4)=[CH:13][N:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

Participants

5

Reactant 2

HCID 104401Iodomethyl pivalateHCID 131722907Potassium (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-5-yl)-1-methyl-1-carbapen-2-em-3-carboxylate

Product 1

HCID 12070022Pivaloyloxymethyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-5-yl)-1-methyl-1-carbapen-2-em-3-carboxylateYield 112.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 40 mg of potassium (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-5-yl)-1-methyl-1-carbapen-2-em-3-carboxylate in 0.8 ml of DMF was added at −30° C. 30 mg of pivaloyloxymethyl iodide, 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 54 mg of the title compound.

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-0e448e43c7c3471a8f8c57b83fecc573
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

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