Phosphoric Acid → HCID 57168106, compound

HRID 1586753Notes

Reaction equation

HRID 1586753 reaction equation
[N:1]1([CH2:9][C@@H:10]2[CH2:14][C@H:13]([S:15][C:16]3[C@H:22]([CH3:23])[C@H:21]4[N:18]([C:19](=[O:27])[C@@H:20]4[C@H:24]([OH:26])[CH3:25])[C:17]=3[C:28]([O:30]CC3C=CC([N+]([O-])=O)=CC=3)=[O:29])[CH2:12][N:11]2C(OCC2C=CC([N+]([O-])=O)=CC=2)=O)[C:8]2[N:4]([N:5]=[CH:6][CH:7]=2)[CH2:3][CH2:2]1.P(=O)(O)(O)O.[H][H]>[OH-].[OH-].[Pd+2].O1CCCC1>[N:1]1([CH2:9][C@@H:10]2[CH2:14][C@H:13]([S:15][C:16]3[C@H:22]([CH3:23])[C@H:21]4[N:18]([C:19](=[O:27])[C@@H:20]4[C@H:24]([OH:26])[CH3:25])[C:17]=3[C:28]([OH:30])=[O:29])[CH2:12][NH:11]2)[C:8]2[N:4]([N:5]=[CH:6][CH:7]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 1004Phosphoric AcidHCID 57104556HCID 57104556, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57168106HCID 57168106, compoundYield 71.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-nitrobenzyl (4R,5S,6S)-3-[(2S,4S)-2-(2,3-dihydro-1H-imidazo[1,2-b]pyrazol-1-yl)methyl-1-(4-nitrobenzyloxycarbonyl) pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.70 g), 20% palladium hydroxide on carbon (0.4 g), 01 M phosphoric acid buffer (pH=6.0, 35 ml) and tetrahydrofuran (35 ml) was stirred for 5 hours under atmospheric pressure of hydrogen at ambient temperature. After the catalyst was filtered off, the filtrate was evaporated in vacuo to remove the organic solvent. The aqueous layer was washed twice with ethyl acetate (30 ml) and evaporated in vacuo to remove the organic solvent. The residue was chromatographed on a nonionic adsorption resin "Diaion HP-20" (20 ml) eluting in turn with water (60 ml) and 5% aqueous acetone [120 ml). The fractions containing the desired compound were collected and lyophilized to give (4R,5S,6S)-3-[(2S,4S)-2-(2,3-dihydro-1H-imidazo[1,2-b]pyrazol-1-yl)methylpyrrolidin-4-yl ]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo [3.2.0]hept-2-ene-2-carboxylic acid (0.29 g).

Workup

  1. filtrationAfter the catalyst was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. customto remove the organic solvent
  4. washThe aqueous layer was washed twice with ethyl acetate (30 ml)
  5. customevaporated in vacuo
  6. customto remove the organic solvent
  7. customThe residue was chromatographed on a nonionic adsorption resin "Diaion
  8. wash" (20 ml) eluting in turn with water (60 ml) and 5% aqueous acetone [120 ml)
  9. additionThe fractions containing the desired compound
  10. customwere collected

Sources & evidence

ORD record
ord-0f862d2dae8342b8af5deb86dc61e70d
Source dataset
uspto-grants-1993_06
Patent number
US05215983

Reaction notes

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