Acetic Acid → HCID 23388261, compound

HRID 1839339Notes

Reaction equation

HRID 1839339 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, compound

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-0bd7af1255d04c3d859abf6d71b9cd08
Source dataset
uspto-grants-2004_01
Patent number
US06677331B2

Reaction notes

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