HCID 131720444, compound → HCID 178465583, compound

HRID 727713Notes

Reaction equation

HRID 727713 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]([CH3:17])[C@H:14]([C:18]([N:20]4[CH2:23][CH:22]([N:24](C(OCC5C=CC([N+]([O-])=O)=CC=5)=O)[C:25](=[NH:27])[CH3:26])[CH2:21]4)=[O:19])[CH2:13]3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].[H][H]>O1CCCC1.O.[Pd]>[C:25]([NH:24][CH:22]1[CH2:21][N:20]([C:18]([C@@H:14]2[CH2:13][C@H:12]([S:11][C:8]3[C@H:9]([CH3:10])[C@@H:5]4[C@@H:4]([C@H:2]([OH:1])[CH3:3])[C:54](=[O:55])[N:6]4[C:7]=3[C:41]([OH:43])=[O:42])[CH2:16][N:15]2[CH3:17])=[O:19])[CH2:23]1)(=[NH:27])[CH3:26]

Participants

6

Reactant 2

HCID 131720444HCID 131720444, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178465583HCID 178465583, compoundYield 61.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

453 mg of 4-nitrobenzyl (1R,5S,6S)-6-[(1R)-1-hydroxyethyl]-1-methyl-2-[(2S,4S)-1-methyl-2-[3-[N-(4-nitrobenzyloxycarbonyl)-N-acetimidoylamino]azetidin-1-ylcarbonyl)pyrrolidin-4-ylthio]-1-carbapen-2-em-3-carboxylate [prepared as described in step (1) above] were dissolved in 21 ml of a 2:1 by volume mixture of tetrahydrofuran and water, and 500 mg of a 10% w/w palladium-on-carbon catalyst were added to the resulting solution. The mixture was then hydrogenated at room temperature for 1.5 hours in an atmosphere of hydrogen. The catalyst was then removed by filtration, and the filtrate was washed with diethyl ether. The aqueous layer was concentrated by evaporation under reduced pressure. The residue was subjected to reverse phase column chromatography (Cosmosil 75C18 -prep, manufactured by Nacalai Tesque, 40 ml). Of the fractions obtained by solution with 8% by volume aqueous acetonitrile, the one containing the title compound was concentrated by evaporation under reduced pressure and freeze-dried, to give 166 mg of the title compound as a powder.

Workup

  1. additionwere added to the resulting solution
  2. customThe catalyst was then removed by filtration
  3. washthe filtrate was washed with diethyl ether
  4. concentrationThe aqueous layer was concentrated by evaporation under reduced pressure
  5. customOf the fractions obtained by solution with 8% by volume aqueous acetonitrile
  6. concentrationthe one containing the title compound was concentrated by evaporation under reduced pressure
  7. customfreeze-dried

Sources & evidence

ORD record
ord-f4ceaa10a3a548f08d1f1fbed4081e48
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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