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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 382639Generated: October 23, 2026

Dichloromethane → Potassium (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-7-yl)-1-methyl-1-carbapen-2-em-3-carboxylate

https://huagongshe.com/en/reaction/382639

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDichloromethaneHCID 6344—
ReactantTriphenylphosphineHCID 11776—
ReactantPotassium 2-ethylhexanoateHCID 23669619—
Reactantallyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-7-yl)-1-methyl-1-carbapen-2-em-3-carboxylateHCID 131722909—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventEthyl AcetateHCID 8857—
ProductPotassium (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-7-yl)-1-methyl-1-carbapen-2-em-3-carboxylateHCID 131722911—

Reaction Steps

To a solution of 117 mg of allyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-7-yl)-1-methyl-1-carbapen-2-em-3-carboxylate in a mixed solvent of 2.5 ml of dichloromethane and 2.5 ml of ethy acetate were added 8.1 mg of triphenylphosphine, 56.5 mg of potassium 2-ethylhexanoate, and 11.8 mg of tetrakis(triphenylphosphine)palladium (0), and the mixture was stirred under the atmosphere of argon at room temperature for 20 minutes. After confirming the exhaustion of the starting materials, the reaction mixture was diluted with 10 ml of ethyl acetate, extracted three or four times with water, and the aqueous layer was concentrated under reduced pressure. The concentrate was purified by column chromatography on COSMOSEAL 40C18-PREP to give the title compound in a yield of 55 mg.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06310056B1
Source datasetuspto-grants-2001_10
ORD IDord-50feba7d8ec4461589af473598174060
Source noteuspto-grants-2001_10