HCID 131721112, compound → HCID 67881963, compound

HRID 362095Notes

Reaction equation

HRID 362095 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:54](=[O:55])[N:6]2[C:7]([C:41]([O:43]CC3C=CC([N+]([O-])=O)=CC=3)=[O:42])=[C:8]([S:11][C@@H:12]3[CH2:16][N:15](C(OCC4C=CC([N+]([O-])=O)=CC=4)=O)[C@H:14]([C:30]([N:32]4[CH2:35][CH:34]([N:36]5[CH:40]=[CH:39][N:38]=[CH:37]5)[CH2:33]4)=[O:31])[CH2:13]3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].[H][H]>O1CCCC1.O.[Pd]>[OH:1][C@@H:2]([C@H:4]1[C:54](=[O:55])[N:6]2[C:7]([C:41]([OH:43])=[O:42])=[C:8]([S:11][C@@H:12]3[CH2:16][NH:15][C@H:14]([C:30]([N:32]4[CH2:33][CH:34]([N:36]5[CH:40]=[CH:39][N:38]=[CH:37]5)[CH2:35]4)=[O:31])[CH2:13]3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

Participants

6

Reactant 2

HCID 131721112HCID 131721112, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67881963HCID 67881963, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.25 g of 4-nitrobenzyl (1R,5S,6S)-6-[(1R)-1-hydroxyethyl]-2-[(2S,4S)-2-[3-(1-imidazolyl)azetidin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio]-1-methyl-1-carbapen-2-em-3-carboxylate [prepared as described in step (1) above] was dissolved in a mixture of 7.5 ml of tetrahydrofuran and 7.5 ml of water, and 0.25 g of a 10% w/w palladium-on-carbon catalyst was added to the resulting solution, after which the mixture was hydrogenated at room temperture for 1.5 hours in an atmosphere of hydrogen. At the end of this time, the catalyst was removed by filtration and the filtrate was washed with diethyl ether. The resulting aqueous layer was then concentrated by evaporation under reduced pressure, and the residue was subjected to reverse phase column chromatography (Cosmosil 75C18 -prep, 30 g, manufactured by Nacalai Tesque). Of the fractions obtained by elution with 7% by volume aqueous acetonitrile, the fraction containing the title compound was concentrated by evaporation under reduced pressure and freeze-dried, to obtain 70 mg of the title compound as a powder.

Workup

  1. additionwas added to the resulting solution
  2. customAt the end of this time, the catalyst was removed by filtration
  3. washthe filtrate was washed with diethyl ether
  4. concentrationThe resulting aqueous layer was then concentrated by evaporation under reduced pressure
  5. customOf the fractions obtained by elution with 7% by volume aqueous acetonitrile

Sources & evidence

ORD record
ord-423917743b94493e9c5af6fc9ebe2ea2
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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