Acetic Acid → HCID 23388261, compound

HRID 989875Notes

Reaction equation

HRID 989875 reaction equation
C(O)(=O)C.O[C@@H]([C@H]1C(=O)N2C(C([O-])=O)=C(C3SC4=C(C(=O)CC)N=CN4C=3)[C@H](C)[C@H]12)C.[Na+].[Si]([O:40][CH2:41][CH2:42][N:43]([CH3:80])[S:44]([C:47]1[N:48]=[CH:49][N:50]2[CH:54]=[C:53]([C:55]3[C@H:56]([CH3:79])[C@@H:57]4[C@@H:74]([C@H:75]([OH:77])[CH3:76])[C:73](=[O:78])[N:58]4[C:59]=3[C:60]([O:62][CH2:63][C:64]3[CH:69]=[CH:68][C:67]([N+:70]([O-:72])=[O:71])=[CH:66][CH:65]=3)=[O:61])[S:52][C:51]=12)(=[O:46])=[O:45])(C(C)(C)C)(C)C.C(=O)([O-])O.[Na+]>C1COCC1>[OH:77][C@@H:75]([C@H:74]1[C:73](=[O:78])[N:58]2[C:59]([C:60]([O:62][CH2:63][C:64]3[CH:65]=[CH:66][C:67]([N+:70]([O-:72])=[O:71])=[CH:68][CH:69]=3)=[O:61])=[C:55]([C:53]3[S:52][C:51]4=[C:47]([S:44](=[O:45])(=[O:46])[N:43]([CH2:42][CH2:41][OH:40])[CH3:80])[N:48]=[CH:49][N:50]4[CH:54]=3)[C@H:56]([CH3:79])[C@H:57]12)[CH3:76]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 23388213HCID 23388213, compoundHCID 23698547HCID 23698547, compound

Product 1

HCID 23388261HCID 23388261, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetic acid (0.36 ml) and 2.0 ml of a 1 M-tetra-n-butylammonium fluoride/THF solution were added under ice cooling to a solution of 273 mg of 4-nitrobenzyl(1S,5R,6S)-2-[7-[N-(2-t-butyldimethylsilyloxyethyl)-N-methylsulfamoyl]imidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate in 8 ml of THF. The mixture was stirred at room temperature for 6 hr. The reaction mixture was added to a dilute aqueous sodium hydrogencarbonate solution, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (dichloromethane:methanol=10:1) to give 175 mg of 4-nitrobenzyl(1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-[7-[N-(2-hydroxyethyl)-N-methyl-sulfamoyl]imidazo[5,1-b]thiazol-2-yl]-1-methyl-1-carbapen-2-em-3-carboxylate.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was removed by distillation
  4. customThe residue was purified by column chromatography on silica gel (dichloromethane:methanol=10:1)

Sources & evidence

ORD record
ord-390b2ecea4e3420bb414d3d4b7368950
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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