HCID 131725008, compound → HCID 69366131, compound

HRID 1072356Notes

Reaction equation

HRID 1072356 reaction equation
FC(F)(F)S([O-])(=O)=O.[N:9]([CH2:12][CH2:13][CH2:14][N+:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([C:23]2[N:24]=[CH:25][N:26]3[CH:30]=[C:29]([C:31]4[C@H:32]([CH3:55])[C@@H:33]5[C@@H:50]([C@H:51]([OH:53])[CH3:52])[C:49](=[O:54])[N:34]5[C:35]=4[C:36]([O:38]CC4C=CC([N+]([O-])=O)=CC=4)=[O:37])[S:28][C:27]=23)=[O:22])[CH:16]=1)=[N+]=[N-]>CO>[NH2:9][CH2:12][CH2:13][CH2:14][N+:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([C:23]2[N:24]=[CH:25][N:26]3[CH:30]=[C:29]([C:31]4[C@H:32]([CH3:55])[C@@H:33]5[C@@H:50]([C@H:51]([OH:53])[CH3:52])[C:49](=[O:54])[N:34]5[C:35]=4[C:36]([O-:38])=[O:37])[S:28][C:27]=23)=[O:22])[CH:16]=1

Participants

3

Reactant 1

HCID 131725008HCID 131725008, compound

Product 1

HCID 69366131HCID 69366131, compoundYield 13.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A reaction was carried out in the same manner as in step b) of Example 1, except that 450 mg of 4-nitrobenzyl (1S,5R,6S)-2-[7-[1-(3-azidopropyl)pyridinium-3-yl]carbonylimidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate trifluoromethanesulfonate was used as the starting compound. The reaction product was subjected to column chromatography on Cosmosil 40C18-PREP (10% aqueous methanol solution). The fraction, which had been eluted earlier, was collected and was then ion exchanged by column chromatography (water) on Amberlyst (A-26) to give 38 mg of the title compound.

Workup

  1. washThe fraction, which had been eluted earlier
  2. customwas collected

Sources & evidence

ORD record
ord-dc53b41535744eea8ca64f9c89aa3ab8
Source dataset
uspto-grants-2005_06
Patent number
US06908913B2

Reaction notes

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