Water → HCID 86591211, compound

HRID 1072350Notes

Reaction equation

HRID 1072350 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].CS(O[C@H:10]1[CH2:14][N:13]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[O:16])[C@H:12]([C:28]([C:30]2[N:31]=[CH:32][N:33]3[CH:37]=[CH:36][S:35][C:34]=23)=[O:29])[CH2:11]1)(=O)=O.O>CN(C=O)C>[N:1]([C@@H:10]1[CH2:14][N:13]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[O:16])[C@H:12]([C:28]([C:30]2[N:31]=[CH:32][N:33]3[CH:37]=[CH:36][S:35][C:34]=23)=[O:29])[CH2:11]1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 86759765HCID 86759765, compound

Product 1

HCID 86591211HCID 86591211, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Sodium azide (87 mg) was added to a solution of 552 mg of 7-[(2S,4R)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-2-yl]carbonylimidazo[5,1-b]thiazole in 5 ml of DMF, and the mixture was stirred at 100° C. for 13 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate, followed by washing three times with brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was then removed by distillation to give 474 mg of a crude product of 7-[(2S,4S)-4-azido-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-2-yl]carbonylimidazo[5,1-b]thiazole.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washby washing three times with brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was then removed by distillation

Sources & evidence

ORD record
ord-fe7e2d4f94b042d0b7f752552176b8ec
Source dataset
uspto-grants-2005_06
Patent number
US06908913B2

Reaction notes

Loading…