Water → HCID 70299392, compound

HRID 382628Notes

Reaction equation

HRID 382628 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:23](=[O:24])[N:6]2[C:7]([C:20]([OH:22])=[O:21])=[C:8]([C:11]3[S:15][C:14]4=[CH:16][N:17]=[C:18]([CH3:19])[N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].O.C(=O)([O-])O.[Na+].[C:31]([O:37][CH2:38]I)(=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33]>CN(C=O)C.C(OCC)(=O)C>[OH:1][C@@H:2]([C@H:4]1[C:23](=[O:24])[N:6]2[C:7]([C:20]([O:22][CH2:38][O:37][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])=[O:21])=[C:8]([C:11]3[S:15][C:14]4=[CH:16][N:17]=[C:18]([CH3:19])[N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 104401Iodomethyl pivalateHCID 516892Sodium BicarbonateHCID 20698508HCID 20698508, compound

Product 1

HCID 70299392HCID 70299392, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 46.8 mg of (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-(5-methylimidazo[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylic acid 5 ml of water was added 134 ml of a 0.1 N aqueous sodium hydrogen carbonate solution. The mixture was lyophilized, dissolved in 1 ml of DMF, added with 0.034 ml of pivaloyloxymethyl iodide under the atmosphere of argon at −30° C., and stirred at the same temperature for 1.5 hours. The reaction mixture was diluted with 50 ml of ethyl acetate, and washed with 50 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 1 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 44.5 mg of the title compound.

Workup

  1. washwashed with 50 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 1 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-d8598bed528a419eab49f519e5a576f1
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

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