2-Fluoroethyl trifluoromethanesulfonate → HCID 178459453, compound

HRID 568250Notes

Reaction equation

HRID 568250 reaction equation
[F:1][C:2]([F:11])([F:10])[S:3]([O:6][CH2:7][CH2:8][F:9])(=[O:5])=[O:4].[CH2:12]([O:15][C:16]([N:18]1[C@H:22]([CH2:23][C:24]2[S:28][C:27]3=[CH:29][N:30]=[C:31]([CH3:32])[N:26]3[CH:25]=2)[CH2:21][C@H:20]([S:33][C:34]2[C@H:35]([CH3:51])[C@@H:36]3[C@@H:46]([C@H:47]([OH:49])[CH3:48])[C:45](=[O:50])[N:37]3[C:38]=2[C:39]([O:41][CH2:42][CH:43]=[CH2:44])=[O:40])[CH2:19]1)=[O:17])[CH:13]=[CH2:14]>>[F:1][C:2]([F:11])([F:10])[S:3]([O-:6])(=[O:5])=[O:4].[CH2:12]([O:15][C:16]([N:18]1[C@H:22]([CH2:23][C:24]2[S:28][C:27]3=[CH:29][N:30]([CH2:7][CH2:8][F:9])[C:31]([CH3:32])=[N+:26]3[CH:25]=2)[CH2:21][C@H:20]([S:33][C:34]2[C@H:35]([CH3:51])[C@@H:36]3[C@@H:46]([C@H:47]([OH:49])[CH3:48])[C:45](=[O:50])[N:37]3[C:38]=2[C:39]([O:41][CH2:42][CH:43]=[CH2:44])=[O:40])[CH2:19]1)=[O:17])[CH:13]=[CH2:14]

Participants

3

Reactant 2

HCID 136389352-Fluoroethyl trifluoromethanesulfonateHCID 131722343Allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-(5-methylimidazo[5,1-b]thiazol-2-yl)methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate

Product 1

HCID 178459453HCID 178459453, compoundYield 89.2%

Procedure

2-Fluoroethyl trifluoromethanesulfonate (40.6 mg) is added to 30.6 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-(5-methylimidazo[5,1-b]thiazol-2-yl)methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate described in Example 31-a), and the mixture is stirred in an argon atmosphere at room temperature for 3.5 hr. The solvent is removed by evaporation under reduced pressure. The residue is purified by column chromatography on Sephadex LH-20 (dichloromethane:methanol=1:1) to give 36.4 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[6-(2-fluoroethyl)-5-methylimidazo[5,1-b]thiazolium-2-yl]methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate trifluoromethanesulfonate as a yellow oil.

Workup

  1. customThe solvent is removed by evaporation under reduced pressure
  2. customThe residue is purified by column chromatography on Sephadex

Sources & evidence

ORD record
ord-c8e7857abf35460485a7eb4770100ded
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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