Methyl triflate → 4-Nitrobenzyl (1s,5r,6s)-6-((1r)-1-hydroxyethyl)-1-methyl-2-[7-(1-methylpyridinium-3-yl)carbonylimidazo-[5,1-b]thiazol-2-yl]-1-carbapen-2-em-3-carboxylate trifluoromethanesulfonate

HRID 1072357Notes

Reaction equation

HRID 1072357 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:40](=[O:41])[N:6]2[C:7]([C:27]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=3)=[O:28])=[C:8]([C:11]3[S:15][C:14]4=[C:16]([C:19]([C:21]5[CH:22]=[N:23][CH:24]=[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:42][C:43]([F:50])([F:49])[S:44]([O:47]C)(=[O:46])=[O:45]>ClCCl>[F:42][C:43]([F:50])([F:49])[S:44]([O-:47])(=[O:46])=[O:45].[OH:1][C@@H:2]([C@H:4]1[C:40](=[O:41])[N:6]2[C:7]([C:27]([O:29][CH2:30][C:31]3[CH:32]=[CH:33][C:34]([N+:37]([O-:39])=[O:38])=[CH:35][CH:36]=3)=[O:28])=[C:8]([C:11]3[S:15][C:14]4=[C:16]([C:19]([C:21]5[CH:22]=[N+:23]([CH3:43])[CH:24]=[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]

Participants

4

Reactant 2

HCID 9526Methyl triflateHCID 68934911(4-nitrobenzyl) (1S,5R,6S)-6-[(1R)-1-hydroxyethyl]-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-1-methylcarbapen-2-em-3-carboxylate

Product 1

HCID 1317250094-Nitrobenzyl (1s,5r,6s)-6-((1r)-1-hydroxyethyl)-1-methyl-2-[7-(1-methylpyridinium-3-yl)carbonylimidazo-[5,1-b]thiazol-2-yl]-1-carbapen-2-em-3-carboxylate trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-1-carbapen-2-em-3-carboxylate (240 mg) was suspended in 10 ml of dichloromethane to prepare a suspension. Methyl trifluoromethanesulfonate (0.047 ml) was added to the suspension, and the mixture was stirred at room temperature for 20 min. The reaction solution was concentrated under the reduced pressure to give 333 mg of 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[7-(1-methylpyridinium-3-yl)carbonylimidazo-[5,1-b]thiazol-2-yl]-1-carbapen-2-em-3-carboxylate trifluoromethanesulfonate.

Workup

  1. customto prepare a suspension
  2. concentrationThe reaction solution was concentrated under the reduced pressure

Sources & evidence

ORD record
ord-ef5f4bdd8ff34bafb7f8ea6f6553875d
Source dataset
uspto-grants-2005_06
Patent number
US06908913B2

Reaction notes

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