Sodium Iodide → HCID 91468330, compound

HRID 1072384Notes

Reaction equation

HRID 1072384 reaction equation
Cl[CH2:2][C:3]([C:5]1[N:6]=[CH:7][N:8]2[CH:12]=[C:11]([C:13]3[C@H:14]([CH3:37])[C@@H:15]4[C@@H:32]([C@H:33]([OH:35])[CH3:34])[C:31](=[O:36])[N:16]4[C:17]=3[C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=3)=[O:19])[S:10][C:9]=12)=[O:4].[I-].[Na+].[NH:40]1[CH2:44][CH2:43][CH2:42][CH2:41]1>CC(C)=O.[Cl-].[Na+].O>[OH:35][C@@H:33]([C@H:32]1[C:31](=[O:36])[N:16]2[C:17]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=3)=[O:19])=[C:13]([C:11]3[S:10][C:9]4=[C:5]([C:3](=[O:4])[CH2:2][N:40]5[CH2:44][CH2:43][CH2:42][CH2:41]5)[N:6]=[CH:7][N:8]4[CH:12]=3)[C@H:14]([CH3:37])[C@H:15]12)[CH3:34]

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 31268PyrrolidineHCID 90945516HCID 90945516, compound

Product 1

HCID 91468330HCID 91468330, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 57417360Sodium chloride; waterSolvent2×

Procedure

4-Nitrobenzyl (1S,5R,6S)-2-(7-chloroacetylimidazo[5,1-b]thiazol-2-yl)-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate (161 mg) was dissolved in 5 ml of acetone to prepare a solution. Sodium iodide (67 mg) was added to the solution, and the mixture was stirred at room temperature for 1.5 hr. Brine was added to the reaction solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate. The solvent was removed by distillation, and the residue was dissolved in 5 ml of N,N-dimethylformamide to prepare a solution. Pyrrolidine (0.03 ml) was added to the solution, and the mixture was stirred at room temperature for 2 hr. Brine was added to the reaction solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate. The solvent was removed by distillation, and the residue was washed with diethyl ether to give 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[7-(pyrrolidin-1-yl)acetylimidazo[5,1-b]thiazol-2-yl]-1-carbapen-2-em-3-carboxylate.

Workup

  1. customto prepare a solution
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation
  5. dissolutionthe residue was dissolved in 5 ml of N,N-dimethylformamide
  6. customto prepare a solution
  7. stirringthe mixture was stirred at room temperature for 2 hr
  8. extractionthe mixture was extracted with ethyl acetate
  9. dry with materialThe extract was dried over anhydrous magnesium sulfate
  10. customThe solvent was removed by distillation
  11. washthe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-e5a8b11a0ed440469f522af631f318ad
Source dataset
uspto-grants-2005_06
Patent number
US06908913B2

Reaction notes

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