Acetic Acid → HCID 90902646, compound

HRID 1072373Notes

Reaction equation

HRID 1072373 reaction equation
C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.[Si]([O:35][C@H:36]1[CH2:40][N:39]([C:41]([O:43][CH2:44][C:45]2[CH:50]=[CH:49][C:48]([N+:51]([O-:53])=[O:52])=[CH:47][CH:46]=2)=[O:42])[C@H:38]([C:54]([C:56]2[N:57]=[CH:58][N:59]3[CH:63]=[C:62]([C:64]4[C@H:65]([CH3:88])[C@@H:66]5[C@@H:83]([C@H:84]([OH:86])[CH3:85])[C:82](=[O:87])[N:67]5[C:68]=4[C:69]([O:71][CH2:72][C:73]4[CH:78]=[CH:77][C:76]([N+:79]([O-:81])=[O:80])=[CH:75][CH:74]=4)=[O:70])[S:61][C:60]=23)=[O:55])[CH2:37]1)(C(C)(C)C)(C)C.C(=O)([O-])O.[Na+]>C1COCC1.[Cl-].[Na+].O>[OH:35][C@H:36]1[CH2:40][N:39]([C:41]([O:43][CH2:44][C:45]2[CH:46]=[CH:47][C:48]([N+:51]([O-:53])=[O:52])=[CH:49][CH:50]=2)=[O:42])[C@H:38]([C:54]([C:56]2[N:57]=[CH:58][N:59]3[CH:63]=[C:62]([C:64]4[C@H:65]([CH3:88])[C@@H:66]5[C@@H:83]([C@H:84]([OH:86])[CH3:85])[C:82](=[O:87])[N:67]5[C:68]=4[C:69]([O:71][CH2:72][C:73]4[CH:74]=[CH:75][C:76]([N+:79]([O-:81])=[O:80])=[CH:77][CH:78]=4)=[O:70])[S:61][C:60]=23)=[O:55])[CH2:37]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 11078149TBAF tetrahydrofuranHCID 91366763HCID 91366763, compound

Product 1

HCID 90902646HCID 90902646, compoundYield 74.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Acetic acid (0.219 ml) and 1.27 ml of a 1 M tetra-n-butylammonium fluoride/THF solution were added to a solution of 369 mg of 4-nitrobenzyl (1S,5R,6S)-2-[7[(2S,4R)-4-t-butyldimethylsilyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-2-yl]carbonylimidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate in 10 ml of THF, and the mixture was stirred at room temperature for 7 hr. Brine was added to the reaction solution. The mixture was adjusted to pH 8.2 by the addition of a saturated sodium hydrogencarbonate solution and was then extracted twice with ethyl acetate. The organic layers were combined, and the combined organic layers were washed with brine and were dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane:methanol=10:1) to give 239 mg of 4-nitrobenzyl (1S,5R,6S)-2-[7-[(2S,4R)-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-2-yl]carbonylimidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate.

Workup

  1. extractionwas then extracted twice with ethyl acetate
  2. washthe combined organic layers were washed with brine
  3. dry with materialwere dried over anhydrous magnesium sulfate
  4. customThe solvent was then removed by distillation under the reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (dichloromethane:methanol=10:1)

Sources & evidence

ORD record
ord-b92d908e4ca8455096a5b21a0af670fc
Source dataset
uspto-grants-2005_06
Patent number
US06908913B2

Reaction notes

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