Phosphate → HCID 18641575, compound

HRID 1088997Notes

Reaction equation

HRID 1088997 reaction equation
[CH3:1][N:2]1[C:6]([S:7][CH2:8][C@@H:9]2[CH2:13][C@H:12]([S:14][C:15]3[C@H:21]([CH3:22])[C@H:20]4[N:17]([C:18](=[O:26])[C@@H:19]4[C@H:23]([OH:25])[CH3:24])[C:16]=3[C:27]([O:29]CC3C=CC([N+]([O-])=O)=CC=3)=[O:28])[CH2:11][N:10]2C(OCC2C=CC([N+]([O-])=O)=CC=2)=O)=[N:5][N:4]=[N:3]1.P([O-])([O-])([O-])=O.[H][H]>[OH-].[OH-].[Pd+2].O1CCCC1>[OH:25][C@@H:23]([C@H:19]1[C:18](=[O:26])[N:17]2[C@@H:20]1[C@@H:21]([CH3:22])[C:15]([S:14][C@@H:12]1[CH2:11][NH:10][C@H:9]([CH2:8][S:7][C:6]3[N:2]([CH3:1])[N:3]=[N:4][N:5]=3)[CH2:13]1)=[C:16]2[C:27]([OH:29])=[O:28])[CH3:24]

Participants

6

Reactant 3

HCID 1061PhosphateHCID 57083059HCID 57083059, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18641575HCID 18641575, compoundYield 49.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-nitrobenzyl (4R,5S,6S)-3-[(2S,4S)-2-(1-methyl-1H-tetrazol-5-yl)thiomethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-yl]thio-4-methyl-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.80 g), 20% palladium hydroxide on carbon (0.5 g), 0.05M phosphate buffer (pH 6.3, 30 ml) and tetrahydrofuran (30 ml) was stirred for 3 hours under atmospheric pressure of hydrogen at ambient temperature. After the catalyst was filtered off, the filtrate was concentrated under reduced pressure to remove the organic solvent. The residue was washed with ethyl acetate (30 ml×2) and evaporated in vacuo to remove the organic solvent. The residue was chromatographed on nonionic adsorption resin "Diaion HP-20" (Trademark, made by Mitsubishi Chemical Industries) (20 ml) eluting in turn with water (60 ml) and 10% aqueous acetone solution (120 ml). The fractions containing the desired compound were collected and lyophilized to give (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[(2S,4S)-2-{(1-methyl-1H-tetrazol-5-yl)thiomethyl}pyrrolidin-4-ylthio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (0.23 g).

Workup

  1. filtrationAfter the catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto remove the organic solvent
  4. washThe residue was washed with ethyl acetate (30 ml×2)
  5. customevaporated in vacuo
  6. customto remove the organic solvent
  7. customThe residue was chromatographed on nonionic adsorption resin "Diaion
  8. wash" (Trademark, made by Mitsubishi Chemical Industries) (20 ml) eluting in turn with water (60 ml) and 10% aqueous acetone solution (120 ml)
  9. additionThe fractions containing the desired compound
  10. customwere collected

Sources & evidence

ORD record
ord-6f257ee217a746fc83d5ce5dfd781640
Source dataset
uspto-grants-1990_10
Patent number
US04963543

Reaction notes

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