Potassium azide → HCID 131715738, compound

HRID 847195Notes

Reaction equation

HRID 847195 reaction equation
[N-:1]=[N+:2]=[N-:3].[K+].[N+](C1C=CC(S(O[C:18]2[CH2:19][C@@H:20]3[CH2:34][C:33](=[O:35])[N:21]3[C:22]=2[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])(=O)=O)=CC=1)([O-])=O>C(OCC)C>[N:1]([C:18]1[CH2:19][C@@H:20]2[CH2:34][C:33](=[O:35])[N:21]2[C:22]=1[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 10290740Potassium azideHCID 131715740HCID 131715740, compound

Product 1

HCID 131715738HCID 131715738, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Potassium azide (3.2 mg, 39 micromol) was added to a stirred, 0° C. solution of benzyl 2-(p-nitrobenzenesulfonyloxy)-carbapen-2-em-3-carboxylate (5.1 mg, 12 micromol) in anhydrous 5:1 (v/v) acetonitriledichloromethane. After 10 min. the mixture was applied to one 10 cm×20 cm 250 micron silica gel thin layer chromatography plate and developed with diethyl ether. The band centered at Rf 0.5 was eluted with ethyl acetate and the eluate was evaporated under vacuum to provide 1.2 mg (37%) benzyl 2-azidocarbapen-2-em-3-carboxylate.

Workup

  1. washwas eluted with ethyl acetate
  2. customthe eluate was evaporated under vacuum

Sources & evidence

ORD record
ord-7a3334dbed654f5386a3838aa74732df
Source dataset
uspto-grants-1992_08
Patent number
US05140030

Reaction notes

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