HCID 15117432, compound → HCID 15117446, compound

HRID 1029692Notes

Reaction equation

HRID 1029692 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:10](=[O:11])[N:9]2[C@@H:5]1[CH2:6][C:7]([C@@H:25]1[CH2:29][S:28][CH2:27][N:26]1C(OCC1C=CC([N+]([O-])=O)=CC=1)=O)=[C:8]2[C:12]([O:14]CC1C=CC([N+]([O-])=O)=CC=1)=[O:13])[CH3:3].[H][H]>O1CCCC1.P([O-])([O-])([O-])=O.[OH-].[OH-].[Pd+2]>[OH:1][C@@H:2]([C@H:4]1[C:10](=[O:11])[N:9]2[C@@H:5]1[CH2:6][C:7]([C@@H:25]1[CH2:29][S:28][CH2:27][NH:26]1)=[C:8]2[C:12]([OH:14])=[O:13])[CH3:3]

Participants

6

Reactant 2

HCID 15117432HCID 15117432, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15117446HCID 15117446, compoundYield 6.3%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 1061PhosphateSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-nitrobenzyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-[(4R)-3-(4-nitrobenzyloxycarbonyl)thiazolidin-4-yl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (2.00 g) in a mixture of tetrahydrofuran (30 ml) and phosphate buffer (pH 6.5) (30 ml) was hydrogenated under atmospheric pressure of hydrogen over palladium hydroxide on carbon (20%, 0.6 g) for 3 hours at ambient temperature. The catalyst was filtered off and the filtrate was concentrated under reduced pressure to give an aqueous solution. The solution was washed with ethyl acetate, subjected to a column chromatography on silica gel (75 g), and eluted with a mixture of acetonitrile and 75:25, V/V). The fractions containing the object compound were collected and lyophilized to give (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-[(4R)-thiazolidin-4-yl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (0.06 g) as a solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto give an aqueous solution
  4. washThe solution was washed with ethyl acetate
  5. washeluted with a mixture of acetonitrile and 75:25, V/V)
  6. additionThe fractions containing the object compound
  7. customwere collected

Sources & evidence

ORD record
ord-7fdd6487e0e94b879d47808f2ca59f18
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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