Ethanol → HCID 70539288, compound

HRID 1719340Notes

Reaction equation

HRID 1719340 reaction equation
O.P([O-])([O-])(O)=O.[K+:7].[K+].C(O)C.[CH3:12][C:13]([C@@H:29]1[C:35](=[O:36])[N:34]2[C@@H:30]1[CH2:31][C:32]([S:50][CH2:51][CH2:52][NH:53]C(OCC1C=CC([N+]([O-])=O)=CC=1)=O)=[C:33]2[C:37]([O:39]CC1C=CC([N+]([O-])=O)=CC=1)=[O:38])([O:15]C(OCC1C=CC([N+]([O-])=O)=CC=1)=O)[CH3:14]>O1CCOCC1.[Pt]=O>[NH2:53][CH2:52][CH2:51][S:50][C:32]1[CH2:31][C@H:30]2[N:34]([C:35](=[O:36])[C@H:29]2[C:13]([OH:15])([CH3:14])[CH3:12])[C:33]=1[C:37]([O-:39])=[O:38].[K+:7]

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 24450Potassium Phosphate, DibasicHCID 53907551HCID 53907551, compound

Product 1

HCID 70539288HCID 70539288, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of platinum oxide (60.0 mg), water (4.2 ml), aqueous dipotassium hydrogen phosphate (1.0M, 0.385 ml) and ethanol (0.6 ml) was shaken for 30 minutes under a hydrogen atmosphere (50 psi) at ambient temperature. The mixture was added to a solution of 4-nitrobenzyl (5R,6R)-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-3-[2-(4-nitrobenzyloxycarbonylamino)-ethylthio]-7-oxo-1-azabicyclo-[3.2.0]hept-2-ene-2-carboxylate (60.0 mg) in dioxane (7.2 ml) and shaken for 2 hours under a hydrogen atmosphere (50 psi) at ambient temperature. The reaction mixture was filtered using diatomaceous earth and the filter-cake was washed with water (20 ml). The combined filtrates (32 ml) were lyophilized over a period of 4 hours. The residue was chromatographed on non-ionic adsorption resin, Diaion HP-20-AG (trade mark, made by Mitsubishi Chemical Industries) (13×230 mm) eluting with water (120 ml) and then a mixture of water and isopropanol (19:1, 60 ml). The fractions showing UV maxima at 296 nm were collected, concentrated and lyophilized to give potassium (5R,6R)-3-(2-aminoethylthio)-6-(1-hydroxy-1-methylethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (10.4 mg) as pale yellow powder.

Workup

  1. stirringshaken for 2 hours under a hydrogen atmosphere (50 psi) at ambient temperature
  2. filtrationThe reaction mixture was filtered
  3. washthe filter-cake was washed with water (20 ml)
  4. waitThe combined filtrates (32 ml) were lyophilized over a period of 4 hours
  5. customThe residue was chromatographed on non-ionic adsorption resin, Diaion HP-20-AG (trade mark, made by Mitsubishi Chemical Industries) (13×230 mm)
  6. washeluting with water (120 ml)
  7. additiona mixture of water and isopropanol (19:1, 60 ml)
  8. customwere collected
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-70345b607bd34c0bb4cb4e1b54ab2580
Source dataset
uspto-grants-1985_09
Patent number
US04539152

Reaction notes

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