Potassium Carbonate → HCID 69364253, compound

HRID 1072348Notes

Reaction equation

HRID 1072348 reaction equation
[Si]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)=[O:15])[C@H:11]([C:27]([C:29]2[N:30]=[CH:31][N:32]3[CH:36]=[C:35]([Sn](CCCC)(CCCC)CCCC)[S:34][C:33]=23)=[O:28])[CH2:10]1)(C(C)(C)C)(C)C.C(=O)([O-])[O-].[K+].[K+]>Cl.CO>[OH:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)=[O:15])[C@H:11]([C:27]([C:29]2[N:30]=[CH:31][N:32]3[CH:36]=[CH:35][S:34][C:33]=23)=[O:28])[CH2:10]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 20802801HCID 20802801, compound

Product 1

HCID 69364253HCID 69364253, compoundYield 146%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

7-[(2S,4R)-4-t-Butyldimethylsilyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-2-yl]carbonyl-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole (1.15 g) was dissolved in 10 ml of a 1.6 N hydrochloric acid/methanol solution to prepare a solution which was stirred under ice cooling for 30 min. An aqueous potassium carbonate solution was added to the reaction solution, and the mixture was extracted with dichloromethane, followed by washing with brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was then removed by distillation to give 853 mg of 7-[(2S,4R)-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-2-yl]carbonylimidazo[5,1-b]thiazole.

Workup

  1. customto prepare a solution which
  2. extractionthe mixture was extracted with dichloromethane
  3. washby washing with brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was then removed by distillation

Sources & evidence

ORD record
ord-486c0af5732f48d2b217417792d75eaa
Source dataset
uspto-grants-2005_06
Patent number
US06908913B2

Reaction notes

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