Water → HCID 23387834, compound

HRID 989885

Reaction equation

HRID 989885 reaction equation
[CH3:1][C:2]([CH3:13])([O:6][C:7]([O:9][CH:10](Cl)[CH3:11])=[O:8])[CH2:3][CH2:4][CH3:5].[OH:14][C@@H:15]([C@H:17]1[C:37](=[O:38])[N:19]2[C:20]([C:34]([O-:36])=[O:35])=[C:21]([C:24]3[S:28][C:27]4=[C:29]([S:32][CH3:33])[N:30]=[CH:31][N:26]4[CH:25]=3)[C@H:22]([CH3:23])[C@H:18]12)[CH3:16].[Na+].O>CN(C=O)C.[Ag]I>[OH:14][C@@H:15]([C@H:17]1[C:37](=[O:38])[N:19]2[C:20]([C:34]([O:36][CH:10]([O:9][C:7]([O:6][C:2]([CH3:13])([CH3:1])[CH2:3][CH2:4][CH3:5])=[O:8])[CH3:11])=[O:35])=[C:21]([C:24]3[S:28][C:27]4=[C:29]([S:32][CH3:33])[N:30]=[CH:31][N:26]4[CH:25]=3)[C@H:22]([CH3:23])[C@H:18]12)[CH3:16]

Participants

6

Reactant 3

HCID 962WaterHCID 23449137HCID 23449137, compoundHCID 23669370HCID 23669370, compound

Product 1

HCID 23387834HCID 23387834, compoundYield 29.9%

Reagents, catalysts & solvents 2

HCID 24563Silver iodideCatalystHCID 6228DimethylformamideSolvent3×

Procedure

A solution of 156.6 mg of 1-(1,1-dimethyl-1-butyloxycarbonyloxy)ethyl chloride in 2.0 ml of DMF was added to a suspension of 176.1 mg of silver iodide in 2.0 ml of DMF. The mixture was stirred in an argon atmosphere at room temperature for one hr. A solution of 200.0 mg of sodium(1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-(7-methylthio-imidazo[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylate in 1.0 ml of DMF was added thereto, followed by stirring for 3 hr. Water (10 ml) was added to the reaction solution to terminate the reaction. The system was extracted three times with 10 ml of ethyl acetate, followed by washing three times with 30 ml of semisaturated brine. The organic layer was dried over anhydrous magnesium sulfate and filtered. The residue was purified by chromatography on silica gel (chloroform:methanol=20:1) to give 82.3 mg of the title compound.

Workup

  1. stirringby stirring for 3 hr
  2. customto terminate
  3. customthe reaction
  4. extractionThe system was extracted three times with 10 ml of ethyl acetate
  5. washby washing three times with 30 ml of semisaturated brine
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe residue was purified by chromatography on silica gel (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-675901b43e19495ab0dd9350190c3749
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Linked notes

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