Water → HCID 13018200, compound

HRID 851627Notes

Reaction equation

HRID 851627 reaction equation
[N+](C1C=CC(C[CH:9]2[C@@H:15]3[N:12]([C:13](=[O:19])[C@@H:14]3[C@@H:16]([OH:18])[CH3:17])[C:11]([C:20]([O-:22])=[O:21])=[C:10]2[S:23][CH2:24][CH2:25][NH:26]C(OCC2C=CC([N+]([O-])=O)=CC=2)=O)=CC=1)([O-])=O.O1CCOCC1.O.P([O-])([O-])([O-])=O>[Pd].C(O)C>[NH2:26][CH2:25][CH2:24][S:23][C:10]1[CH2:9][C@H:15]2[N:12]([C:13](=[O:19])[C@@H:14]2[C@@H:16]([OH:18])[CH3:17])[C:11]=1[C:20]([OH:22])=[O:21]

Participants

7

Reactant 4

HCID 962WaterHCID 1061PhosphateHCID 312751,4-DioxaneHCID 131712997HCID 131712997, compound

Product 1

HCID 13018200HCID 13018200, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of the ester (e3) (30 mg), 10% palladium on charcoal (50 mg), dioxan (4 ml), water (1 ml), ethanol (0.3 ml) and 0.05 M pH 7 phosphate buffer solution (1.3 ml) was shaken under hydrogen for 2h. The catalyst was removed by filtration of the mixture over Celite washing with water (10 ml) and the solution was then concentrated to a volume of about 10 ml. The aqueous solution was washed with ether (3×20 ml) and ethyl acetate (10 ml) before concentrating in vacuo to a volume of about 3 ml. The solution was loaded onto a column (80×12 mm) of XAD-2, which was then eluted with water to afford (5R, 6S)-3-(2-aminoethylthio)-6-[(s)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (e4) which was identified by the absorption at λmax (H2O) 297 nm in the uv spectrum.

Workup

  1. customThe catalyst was removed by filtration of the mixture over Celite
  2. washwashing with water (10 ml)
  3. concentrationthe solution was then concentrated to a volume of about 10 ml
  4. washThe aqueous solution was washed with ether (3×20 ml) and ethyl acetate (10 ml)
  5. concentrationbefore concentrating in vacuo to a volume of about 3 ml
  6. washwas then eluted with water

Sources & evidence

ORD record
ord-f815945d8a5e40b389605d07f41829ab
Source dataset
uspto-grants-1983_05
Patent number
US04386029

Reaction notes

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