Methyl triflate → HCID 131725010, compound

HRID 1072371Notes

Reaction equation

HRID 1072371 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:41](=[O:42])[N:6]2[C:7]([C:28]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=3)=[O:29])=[C:8]([C:11]3[S:15][C:14]4=[C:16]([C:19]([C:21]5[CH:22]=[N:23][C:24]([CH3:27])=[CH:25][CH:26]=5)=[O:20])[N:17]=[CH:18][N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].[F:43][C:44]([F:51])([F:50])[S:45]([O:48]C)(=[O:47])=[O:46]>ClCCl>[F:43][C:44]([F:51])([F:50])[S:45]([O-:48])(=[O:47])=[O:46].[CH3:44][N+:23]1[C:24]([CH3:27])=[CH:25][CH:26]=[C:21]([C:19]([C:16]2[N:17]=[CH:18][N:13]3[CH:12]=[C:11]([C:8]4[C@H:9]([CH3:10])[C@@H:5]5[C@@H:4]([C@H:2]([OH:1])[CH3:3])[C:41](=[O:42])[N:6]5[C:7]=4[C:28]([O:30][CH2:31][C:32]4[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=4)=[O:29])[S:15][C:14]=23)=[O:20])[CH:22]=1

Participants

4

Reactant 2

HCID 9526Methyl triflateHCID 91492839HCID 91492839, compound

Product 1

HCID 131725010HCID 131725010, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under ice cooling, 92 mg of 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[7-(6-methylpyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-1-carbapen-2-em-3-carboxylate was dissolved in 4 ml of dichloromethane to prepare a solution, and 0.018 ml of methyl trifluoromethanesulfonate was added to the solution. The mixture was stirred at that temperature for 30 min. The reaction solution was then concentrated under the reduced pressure to give 110 mg of 4-nitrobenzyl (1S,5R,6S)-2-[7-(1,6-dimethylpyridinium-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate trifluoromethanesulfonate.

Workup

  1. additionwas added to the solution
  2. concentrationThe reaction solution was then concentrated under the reduced pressure

Sources & evidence

ORD record
ord-0b46af2a88d94c18ac1902bed8647680
Source dataset
uspto-grants-2005_06
Patent number
US06908913B2

Reaction notes

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