Hydrochloric Acid → HCID 67618748, compound

HRID 727611Notes

Reaction equation

HRID 727611 reaction equation
[N+](C1C=CC(C[O:9][C:10]([CH2:12][N:13]2[CH2:19][CH2:18][CH2:17][N:16]([C:20]([C@@H:22]3[CH2:26][C@H:25]([S:27][C:28]4[C@H:29]([CH3:52])[C@@H:30]5[C@@H:47]([C@H:48]([OH:50])[CH3:49])[C:46](=[O:51])[N:31]5[C:32]=4[C:33]([O:35]CC4C=CC([N+]([O-])=O)=CC=4)=[O:34])[CH2:24][N:23]3C(OCC3C=CC([N+]([O-])=O)=CC=3)=O)=[O:21])[CH2:15][CH2:14]2)=[O:11])=CC=1)([O-])=O.O1CCCC1.Cl>O>[C:10]([CH2:12][N:13]1[CH2:19][CH2:18][CH2:17][N:16]([C:20]([C@@H:22]2[CH2:26][C@H:25]([S:27][C:28]3[C@H:29]([CH3:52])[C@@H:30]4[C@@H:47]([C@H:48]([OH:50])[CH3:49])[C:46](=[O:51])[N:31]4[C:32]=3[C:33]([OH:35])=[O:34])[CH2:24][NH:23]2)=[O:21])[CH2:15][CH2:14]1)([OH:11])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 10843537HCID 10843537, compound

Product 1

HCID 67618748HCID 67618748, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 0.5 g of 4-nitrobenzyl (1R, 5S, 6S)-2-[(2S, 4S)-2-[4-(4-nitrobenzyloxycarbonylmethyl)-1-homopiperazinylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate [prepared as described in step (a) above] in 15 ml of a 1:1 by volume mixture of tetrahydrofuran and water was mixed with 0.26 ml of 1N aqueous hydrochloric acid, and the mixture was hydrogenated by bubbling hydrogen through it at room temperature for 90 minutes in the presence of 0.5 g of 10% w/w palladium-on-charcoal. The catalyst was then removed by filtration, and the filtrate was washed with diethyl ether. The washed aqueous solution was then concentrated by evaporation under reduced pressure, and the concentrate was purified by reverse phase column chromatography through a Lobar column (Merck, LiChroprep RP-8, size B), using 1% v/v aqueous methanol as the eluent. Those fractions containing the title compound were collected, concentrated by evaporation under reduced pressure and lyophilized, to give 170 mg of the title compound as a powder.

Workup

  1. customby bubbling hydrogen through it at room temperature for 90 minutes in the presence of 0.5 g of 10% w/w palladium-on-charcoal
  2. customThe catalyst was then removed by filtration
  3. washthe filtrate was washed with diethyl ether
  4. concentrationThe washed aqueous solution was then concentrated by evaporation under reduced pressure
  5. customthe concentrate was purified by reverse phase column chromatography through a Lobar column (Merck, LiChroprep RP-8, size B)
  6. additionThose fractions containing the title compound
  7. customwere collected
  8. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-5c66cc6752474df7b2af1dd1b8e20d89
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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