HCID 15056065, compound → HCID 57007843, compound

HRID 1650863Notes

Reaction equation

HRID 1650863 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:10](=[O:11])[N:9]2[C@@H:5]1[C@@H:6]([CH3:64])[C:7]([S:25][C@@H:26]1[CH2:30][N:29](C(OCC3C=CC([N+]([O-])=O)=CC=3)=O)[C@H:28]([CH2:44][N:45]3[CH2:50][CH2:49][N:48](C(OCC4C=CC([N+]([O-])=O)=CC=4)=O)[CH2:47][CH2:46]3)[CH2:27]1)=[C:8]2[C:12]([O:14]CC1C=CC([N+]([O-])=O)=CC=1)=[O:13])[CH3:3].C([O-])(=O)C.[Na+].C(O)(=O)C.[H][H]>[OH-].[OH-].[Pd+2].O1CCCC1>[OH:1][C@@H:2]([C@H:4]1[C:10](=[O:11])[N:9]2[C@@H:5]1[C@@H:6]([CH3:64])[C:7]([S:25][C@@H:26]1[CH2:30][NH:29][C@H:28]([CH2:44][N:45]3[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]3)[CH2:27]1)=[C:8]2[C:12]([OH:14])=[O:13])[CH3:3]

Participants

6

Reactant 3

HCID 15056065HCID 15056065, compoundHCID 23662384Sodium DiacetateHCID 178418361HCID 178418361, compound

Product 1

HCID 57007843HCID 57007843, compoundYield 42.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-nitrobenzyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[(2S,4S)-1-(4-nitrobenzyloxycarbonyl)-2-{4-(4-nitrobenzyloxycarbonyl)piperazin-1-yl}methylpyrrolidin-4-yl]thio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (1.20 g), 20 % palladium hydroxide on carbon (0.6 g), 0.2M sodium acetate-acetic acid buffer (pH=5.8, 50 ml) and tetrahydrofuran (50 ml) was stirred for 5 hours under atmospheric pressure of hydrogen at ambient temperature. After the catalyst was filtered off, the filtrate was evaporated under reduced pressure to remove the organic solvent. The residue was chromatographed on nonionic adsorption resin, "Diaion HP-20" (trademark, made by Mitsubishi Chemical Industries) (30 ml) eluting in turn with water (80 ml) and 5% aqueous acetone (90 ml). The fractions containing the desired compound were collected and lyophilized to give (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[(2S,4S)-2-(piperazin-1-yl)methylpyrrolidin-4-yl]thio-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (0.23 g).

Workup

  1. filtrationAfter the catalyst was filtered off
  2. customthe filtrate was evaporated under reduced pressure
  3. customto remove the organic solvent
  4. customThe residue was chromatographed on nonionic adsorption resin, "Diaion
  5. wash" (trademark, made by Mitsubishi Chemical Industries) (30 ml) eluting in turn with water (80 ml) and 5% aqueous acetone (90 ml)
  6. additionThe fractions containing the desired compound
  7. customwere collected

Sources & evidence

ORD record
ord-0fe45c93db5042808de7c72ab417108a
Source dataset
uspto-grants-1990_05
Patent number
US04925838

Reaction notes

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