Ethyl Acetate → HCID 23388045, compound

HRID 989873Notes

Reaction equation

HRID 989873 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:26](=[O:27])[N:6]2[C:7]([C:23]([O-:25])=[O:24])=[C:8]([C:11]3[S:15][C:14]4=[C:16]([C:19](=[O:22])[CH2:20][CH3:21])[N:17]=[CH:18][N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].[Na+].C(=O)([O-])O.[Na+].[C:34]([O:40][CH2:41]I)(=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36].C(OCC)(=O)C>CN(C=O)C>[OH:1][C@@H:2]([C@H:4]1[C:26](=[O:27])[N:6]2[C:7]([C:23]([O:25][CH2:41][O:40][C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36])=[O:24])=[C:8]([C:11]3[S:15][C:14]4=[C:16]([C:19](=[O:22])[CH2:20][CH3:21])[N:17]=[CH:18][N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 104401Iodomethyl pivalateHCID 516892Sodium BicarbonateHCID 23698547HCID 23698547, compound

Product 1

HCID 23388045HCID 23388045, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium(1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-(7-propionylimidazo[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylate (75.8 mg) was dissolved in 7 ml of DMF. Sodium hydrogencarbonate (4.9 mg) and 0.038 ml of pivaloyloxymethyl iodide were added to the solution in an argon atmosphere at −30° C. The mixture was stirred for 1.5 hr. Ethyl acetate (50 ml) was added to the reaction solution. The mixture was washed three times with 30 ml of semisaturated brine. The organic layer was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated to 5 ml under the reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane:methanol=30:1) to give 62.3 mg of the title compound.

Workup

  1. washThe mixture was washed three times with 30 ml of semisaturated brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated to 5 ml under the reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (dichloromethane:methanol=30:1)

Sources & evidence

ORD record
ord-6cdaae1812b74295a5e1f08a717158e9
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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