Acetic Acid → HCID 23388279, compound

HRID 989874Notes

Reaction equation

HRID 989874 reaction equation
C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.[Si]([O:35][CH2:36][C:37]([C:39]1[N:40]=[CH:41][N:42]2[CH:46]=[C:45]([C:47]3[CH2:48][C@@H:49]4[C@@H:66]([C@H:67]([OH:69])[CH3:68])[C:65](=[O:70])[N:50]4[C:51]=3[C:52]([O:54][CH2:55][C:56]3[CH:61]=[CH:60][C:59]([N+:62]([O-:64])=[O:63])=[CH:58][CH:57]=3)=[O:53])[S:44][C:43]=12)=[O:38])(C(C)(C)C)(C)C.C(=O)([O-])O.[Na+]>C1COCC1.[Cl-].[Na+].O>[OH:35][CH2:36][C:37]([C:39]1[N:40]=[CH:41][N:42]2[CH:46]=[C:45]([C:47]3[CH2:48][C@@H:49]4[C@@H:66]([C@H:67]([OH:69])[CH3:68])[C:65](=[O:70])[N:50]4[C:51]=3[C:52]([O:54][CH2:55][C:56]3[CH:61]=[CH:60][C:59]([N+:62]([O-:64])=[O:63])=[CH:58][CH:57]=3)=[O:53])[S:44][C:43]=12)=[O:38]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 11078149TBAF tetrahydrofuranHCID 23388284HCID 23388284, compound

Product 1

HCID 23388279HCID 23388279, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Acetic acid (0.345 ml) and 2.04 ml of a 1 M tetra-n-butylammonium fluoride/THF solution were added to a solution of 255 mg of 4-nitrobenzyl(5R,6S)-2-(7-t-butyldimethylsilyloxyacetylimidazo[5,1-b]thiazol-2-yl)-6-((1R)-1-hydroxyethyl)-1-carbapen-2-em-3-carboxylate in 8 ml of THF. The mixture was stirred at room temperature for 3 hr. Brine was added to the reaction solution. The mixture was adjusted to pH 8.1 by the addition of a saturated sodium hydrogencarbonate solution, and extracted twice with ethyl acetate. The organic layers were combined, washed twice with brine, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure. Diethylether(5 ml) was added to the residue. The insoluble was collected by filtration to give 196 mg of 4-nitrobenzyl(5R,6S)-2-(7-hydroxyacetylimidazo[5,1-b]thiazol-2-yl)-6-((1R)-1-hydroxyethyl)-1-carbapen-2-em-3-carboxylate.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washwashed twice with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under the reduced pressure
  5. additionDiethylether(5 ml) was added to the residue
  6. filtrationThe insoluble was collected by filtration

Sources & evidence

ORD record
ord-559ae44d9f27463ab1b7c341adac6ba0
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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