Acetic Acid → HCID 23388279, compound

HRID 1839338Notes

Reaction equation

HRID 1839338 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. Diethyl ether(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. additionDiethyl ether(5 ml) was added to the residue
  6. filtrationThe insoluble was collected by filtration

Sources & evidence

ORD record
ord-c42eb869bef642a9a2e5b9f4f83d0217
Source dataset
uspto-grants-2004_01
Patent number
US06677331B2

Reaction notes

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