1,1-Dichloroethane → HCID 178459464, compound
Reaction equation
FC(F)(F)S(O[CH2:7][CH2:8][F:9])(=O)=O.[CH2:12]([O:15][C:16]([N:18]1[C@H:22](/[CH:23]=[CH:24]\[C:25]2[N:26]3[CH:32]=[N:31][CH:30]=[C:27]3[S:28][CH:29]=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].[Cl:52]C(Cl)C>>[Cl-:52].[CH2:12]([O:15][C:16]([N:18]1[C@H:22](/[CH:23]=[CH:24]\[C:25]2[N+:26]3[C:27](=[CH:30][N:31]([CH2:7][CH2:8][F:9])[CH:32]=3)[S:28][CH:29]=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
Procedure
2-Fluoroethyl trifluoromethanesulfonate (198.9 mg) is added to a solution of 53.1 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[2(Z)-(imidazo[5,1-b]thiazol-3-yl)ethenyl]pyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate, described in Example 38-a), in 0.8 ml of dry dichloroethane, and the mixture is stirred in an argon atmosphere at room temperature for 24 hr. The solvent is removed by evaporation under reduced pressure, and the residue is purified by column chromatography on Sephadex LH-20 (dichloromethane:methanol=1:1) and ion-exchanged using Amberlyst A-26 (Cl− form) (water) to give 63.7 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[2(Z)-(6-(2-fluoroethyl)imidazo[5,1-b]thiazolium-3-yl)ethenyl]pyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate chloride as a yellow oil.
Workup
- customThe solvent is removed by evaporation under reduced pressure
- customthe residue is purified by column chromatography on Sephadex
Sources & evidence
- ORD record
- ord-83e8535c0b634bfd89c9857de10c4c9c
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06180622B2
Reaction notes
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