Acetic Acid → HCID 90875098, compound

HRID 1072364Notes

Reaction equation

HRID 1072364 reaction equation
C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.[Si]([O:35][CH2:36][C:37]1[CH:38]=[C:39]([C:43]([C:45]2[N:46]=[CH:47][N:48]3[CH:52]=[C:51]([C:53]4[C@H:54]([CH3:77])[C@@H:55]5[C@@H:72]([C@H:73]([OH:75])[CH3:74])[C:71](=[O:76])[N:56]5[C:57]=4[C:58]([O:60][CH2:61][C:62]4[CH:67]=[CH:66][C:65]([N+:68]([O-:70])=[O:69])=[CH:64][CH:63]=4)=[O:59])[S:50][C:49]=23)=[O:44])[CH:40]=[N:41][CH:42]=1)(C(C)(C)C)(C)C.O>C1COCC1>[OH:75][C@@H:73]([C@H:72]1[C:71](=[O:76])[N:56]2[C:57]([C:58]([O:60][CH2:61][C:62]3[CH:67]=[CH:66][C:65]([N+:68]([O-:70])=[O:69])=[CH:64][CH:63]=3)=[O:59])=[C:53]([C:51]3[S:50][C:49]4=[C:45]([C:43]([C:39]5[CH:40]=[N:41][CH:42]=[C:37]([CH2:36][OH:35])[CH:38]=5)=[O:44])[N:46]=[CH:47][N:48]4[CH:52]=3)[C@H:54]([CH3:77])[C@H:55]12)[CH3:74]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 11078149TBAF tetrahydrofuranHCID 91126976HCID 91126976, compound

Product 1

HCID 90875098HCID 90875098, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under ice cooling, 0.092 ml of acetic acid and 0.799 ml of a 1 M tetra-n-butylammonium fluoride/THF solution were added to a solution of 563 mg of 4-nitrobenzyl (1S,5R,6S)-2-[7-[5-(t-butyldimethylsilyloxymethyl)pyridin-3-yl]carbonylimidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate in 8 ml of THF, and the mixture was stirred for 6 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate, followed by washing with brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was then removed by distillation. The residue was purified by column chromatography (dichloromethane:methanol=1:1) on Sephadex LH-20 to give 435 mg of 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-[7-[5-(hydroxymethyl)pyridin-3-yl]carbonylimidazo[5,1-b]thiazol-2-yl]-1-methyl-1-carbapen-2-em-3-carboxylate.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washby washing with brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was then removed by distillation
  5. customThe residue was purified by column chromatography (dichloromethane:methanol=1:1) on Sephadex

Sources & evidence

ORD record
ord-9c440b5cdd934314b371fc1c1cb27d06
Source dataset
uspto-grants-2005_06
Patent number
US06908913B2

Reaction notes

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