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

HRID 382639

Reaction equation

HRID 382639 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:25](=[O:26])[N:6]2[C:7]([C:19]([O:21]CC=C)=[O:20])=[C:8]([C:11]3[N:12]=[CH:13][N:14]4[CH:18]=[CH:17][S:16][C:15]=34)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].ClCCl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(C(CCCC)C([O-])=O)C.[K+:59]>C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:1][C@@H:2]([C@H:4]1[C:25](=[O:26])[N:6]2[C:7]([C:19]([O-:21])=[O:20])=[C:8]([C:11]3[N:12]=[CH:13][N:14]4[CH:18]=[CH:17][S:16][C:15]=34)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].[K+:59]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11776TriphenylphosphineHCID 23669619Potassium 2-ethylhexanoateHCID 131722909allyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-7-yl)-1-methyl-1-carbapen-2-em-3-carboxylate

Product 1

HCID 131722911Potassium (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-7-yl)-1-methyl-1-carbapen-2-em-3-carboxylate

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

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.

Workup

  1. extractionextracted three or four times with water
  2. concentrationthe aqueous layer was concentrated under reduced pressure
  3. customThe concentrate was purified by column chromatography on COSMOSEAL 40C18-PREP

Sources & evidence

ORD record
ord-50feba7d8ec4461589af473598174060
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Linked notes

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