2-((tert-Butyldimethylsilyl)oxy)ethyl trifluoromethanesulfonate → allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[6-(2-t-butyldimethylsilyloxyethyl)imidazo[5,1-b]thiazolium-2-yl]methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate trifluoromethanesulfonate

HRID 568242Notes

Reaction equation

HRID 568242 reaction equation
[F:1][C:2]([F:18])([F:17])[S:3]([O:6][CH2:7][CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])(=[O:5])=[O:4].[CH2:19]([O:22][C:23]([N:25]1[C@H:29]([CH2:30][C:31]2[S:35][C:34]3=[CH:36][N:37]=[CH:38][N:33]3[CH:32]=2)[CH2:28][C@H:27]([S:39][C:40]2[C@H:41]([CH3:57])[C@@H:42]3[C@@H:52]([C@H:53]([OH:55])[CH3:54])[C:51](=[O:56])[N:43]3[C:44]=2[C:45]([O:47][CH2:48][CH:49]=[CH2:50])=[O:46])[CH2:26]1)=[O:24])[CH:20]=[CH2:21]>ClC(Cl)C>[F:1][C:2]([F:18])([F:17])[S:3]([O-:6])(=[O:5])=[O:4].[CH2:19]([O:22][C:23]([N:25]1[C@H:29]([CH2:30][C:31]2[S:35][C:34]3=[CH:36][N:37]([CH2:7][CH2:8][O:9][Si:10]([C:13]([CH3:14])([CH3:15])[CH3:16])([CH3:11])[CH3:12])[CH:38]=[N+:33]3[CH:32]=2)[CH2:28][C@H:27]([S:39][C:40]2[C@H:41]([CH3:57])[C@@H:42]3[C@@H:52]([C@H:53]([OH:55])[CH3:54])[C:51](=[O:56])[N:43]3[C:44]=2[C:45]([O:47][CH2:48][CH:49]=[CH2:50])=[O:46])[CH2:26]1)=[O:24])[CH:20]=[CH2:21]

Participants

4

Reactant 2

HCID 156781072-((tert-Butyldimethylsilyl)oxy)ethyl trifluoromethanesulfonateHCID 131722333HCID 131722333, compound

Product 1

HCID 178459460allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[6-(2-t-butyldimethylsilyloxyethyl)imidazo[5,1-b]thiazolium-2-yl]methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

2-(t-Butyldimethylsilyloxy)ethyl trifluoromethanesulfonate (20.9 mg) is added to a solution of 32.3 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-(imidazo[5,1-b]thiazol-2-yl)methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate described in Example 23-a) in 0.5 ml of dry dichloroethane, and the mixture is stirred in an argon atmosphere at room temperature for 2 hr. The excess reagent is removed by evaporation under reduced pressure to give allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[6-(2-t-butyldimethylsilyloxyethyl)imidazo[5,1-b]thiazolium-2-yl]methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate trifluoromethanesulfonate as a brown viscous material.

Workup

  1. customThe excess reagent is removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-fc6e3c8954ef47e5a65a42c53b511ddf
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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