HCID 131720443, compound → HCID 178465581, compound

HRID 727712Notes

Reaction equation

HRID 727712 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:66](=[O:67])[N:6]2[C:7]([C:53]([O:55]CC3C=CC([N+]([O-])=O)=CC=3)=[O:54])=[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](C(OCC5C=CC([N+]([O-])=O)=CC=5)=O)[C:37](=[NH:39])[CH3:38])[CH2:33]4)=[O:31])[CH2:13]3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].[H][H]>O1CCCC1.O.[Pd]>[C:37]([NH:36][CH:34]1[CH2:33][N:32]([C:30]([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:66](=[O:67])[N:6]4[C:7]=3[C:53]([OH:55])=[O:54])[CH2:16][NH:15]2)=[O:31])[CH2:35]1)(=[NH:39])[CH3:38]

Participants

6

Reactant 2

HCID 131720443HCID 131720443, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178465581HCID 178465581, compoundYield 35.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.77 g of 4-nitrobenzyl (1R,5S,6S)-6-[(1R)-1-hydroxyethyl]-1-methyl-2-[(2S,4S)-2-{3-[N(4-nitrobenzyloxycarbonyl)-N-acetimidoylamino]azetidin-1-ylcarbonyl}-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio]-1-carbapen-2-em-3-carboxylate [prepared as described in step (1) above] was dissolved in 15 ml of a 2:1 by volume mixture of tetrahydrofuran and water. 0.77 g of a 10% w/w palladium-on-carbon catalyst was then added to the resulting solution, after which the mixture was hydrogenated at room temperature for 2 hours in a hydrogen atmosphere. At the end of this time, the catalyst was removed by filtration, and the filtrate was washed with diethyl ether. The aqueous layer was then concentrated by evaporation under reduced pressure, and the resulting residue was subjected to reverse phase column chromatography (Cosmosil 75C18 -prep, manufactured by Nacalai Tesque, 100 ml). The fraction containing the title compound and obtained by elution with 4% by volume aqueous acetonitrile was concentrated by evaporation under reduced pressure and freeze-dried, to give 0.13 g of the title compound as a powder.

Workup

  1. customAt the end of this time, the catalyst was removed by filtration
  2. washthe filtrate was washed with diethyl ether
  3. concentrationThe aqueous layer was then concentrated by evaporation under reduced pressure
  4. additionThe fraction containing the title compound
  5. customobtained by elution with 4% by volume aqueous acetonitrile
  6. concentrationwas concentrated by evaporation under reduced pressure
  7. customfreeze-dried

Sources & evidence

ORD record
ord-cb271c76090d4c91b3f3cabed15b00fd
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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