HCID 54522479, compound → HCID 131713826, compound

HRID 2418714Notes

Reaction equation

HRID 2418714 reaction equation
[N+](C1C=CC(COC(NCCOC(C=CS[C:21]2[CH2:27][C@H:26]3[N:23]([C:24](=[O:31])[C@H:25]3[C@@H:28]([OH:30])[CH3:29])[C:22]=2[C:32]([O:34]CC2C=CC([N+]([O-])=O)=CC=2)=[O:33])=O)=O)=CC=1)([O-])=O.[H][H]>O1CCOCC1.P([O-])([O-])([O-])=O.[Pd]>[OH:30][C@H:28]([CH:25]1[C:24](=[O:31])[N:23]2[CH:26]1[CH2:27][CH:21]=[C:22]2[C:32]([OH:34])=[O:33])[CH3:29]

Participants

6

Reactant 2

HCID 54522479HCID 54522479, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131713826HCID 131713826, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 1061PhosphateSolventHCID 312751,4-DioxaneSolvent

Procedure

The ester (e29) (150 mg) was dissolved in a mixture of dioxan (10 ml) and 0.05 M pH7 phosphate buffer (4.5 ml), and the solution was shaken with 5% palladium on charcoal (200 mg) in an atmosphere of hydrogen for 2 hours. The mixture was filtered over Celite, washed with water (20 ml), and the solution was then concentrated in vacuo to a volume of ca. 20 ml. The solution was washed with ethyl acetate (4×25 ml), and was then freeze-dried to afford (5R,6R)-3-[2-(Z)-2-aminoethoxycarbonyl)ethenylthio]-6-[(S)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (e30) as a solid; λmax. (H2O) 325 nm., σmax. (KBr) 1750, 1690 and 1565-1610 (br) cm-1. (The product contained ca. 5% of the corresponding E-isomer).

Workup

  1. filtrationThe mixture was filtered over Celite
  2. washwashed with water (20 ml)
  3. concentrationthe solution was then concentrated in vacuo to a volume of ca. 20 ml
  4. washThe solution was washed with ethyl acetate (4×25 ml)
  5. customwas then freeze-dried

Sources & evidence

ORD record
ord-5eefe60b21a14194be4a06e67bd1cd4b
Source dataset
uspto-grants-1984_09
Patent number
US04473578

Reaction notes

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