Ethanol → HCID 70508802, compound

HRID 1903705Notes

Reaction equation

HRID 1903705 reaction equation
[C:1]([NH:4]/[CH:5]=[CH:6]/[S:7][C:8]1[CH2:14][C@H:13]2[N:10]([C:11](=[O:20])[C@@H:12]2[C@H:15]([N:17]=[N+]=[N-])[CH3:16])[C:9]=1[C:21]([O:23]CC1C=CC([N+]([O-])=O)=CC=1)=[O:22])(=[O:3])[CH3:2].O.C(O)C.P([O-])([O-])([O-])=O>O1CCOCC1.[Pd]>[C:1]([NH:4]/[CH:5]=[CH:6]/[S:7][C:8]1[CH2:14][C@H:13]2[N:10]([C:11](=[O:20])[C@@H:12]2[C@H:15]([NH2:17])[CH3:16])[C:9]=1[C:21]([OH:23])=[O:22])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 1061PhosphateHCID 12849731HCID 12849731, compound

Product 1

HCID 70508802HCID 70508802, compoundYield 19.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

The azido derivative (e2) (15 mg) was dissolved in 1,4-dioxan (4 ml), water (0.6 ml), ethanol (0.15 ml) and 0.05 M pH 7.0 phosphate buffer (0.75 ml) and hydrogenated in the presence of 5% palladium on carbon (25 mg) catalyst for 2 hours. The suspension was filtered over Celite, washing well with water (25 ml). The filtrate was concentrated to about 20 ml and washed with ethyl acetate (3×50 ml). The aqueous solution was further concentrated to approximately 5 ml and chromatographed over Biogel P2, eluting with water. Fractions containing the title compound (e3) were identified by the chromophore at λmax (H2O) 307 nm in the uv spectrum and were combined to yield an aqueous solution of the product (1.9 mg), λmax (H2O) 307 nm, 230 nm.

Workup

  1. filtrationThe suspension was filtered over Celite
  2. washwashing well with water (25 ml)
  3. concentrationThe filtrate was concentrated to about 20 ml
  4. washwashed with ethyl acetate (3×50 ml)
  5. concentrationThe aqueous solution was further concentrated to approximately 5 ml
  6. customchromatographed over Biogel P2
  7. washeluting with water
  8. additionFractions containing the title compound (e3)

Sources & evidence

ORD record
ord-e442cc7b498445519737d22ac020ea1e
Source dataset
uspto-grants-1984_03
Patent number
US04438036

Reaction notes

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