HCID 178418361, compound → HCID 178435579, compound

HRID 1647042Notes

Reaction equation

HRID 1647042 reaction equation
[CH2:1]([C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8]([CH3:10])[NH:9][C:5]=2[C:4]=1[N:13]1[CH2:17][CH:16]([CH2:18][N:19]=[N+]=[N-])[O:15][C:14]1=[O:22])[CH3:2].[H][H]>[Pd].C(OCC)(=O)C>[CH2:1]([C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8]([CH3:10])[NH:9][C:5]=2[C:4]=1[N:13]1[CH2:17][CH:16]([CH2:18][NH2:19])[O:15][C:14]1=[O:22])[CH3:2]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178435578HCID 178435578, compound

Product 1

HCID 178435579HCID 178435579, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (±)-3-(5'-1-ethyl-2-methylbenzimidazolyl)-5-(azidomethyl)oxazolidin-2-one (XXXIX, EXAMPLE 70, 0.190 g) and palladium on carbon (10%, 0.065 g) is stirred in ethyl acetate (70 ml) for 15.5 hrs under 1 atm (balloon) hydrogen. The mixture is then filtered and the filtrate concentrated to give the crude product as a solid in an oil. The crude sample is placed on a silica gel column (5 cm×0.5 cm, 40-63μ) and eluted with ethyl acetate followed by methanol/ethyl acetate mixtures (1/9 10 ml, 1/3 20 ml, 1/1 20 ml. The 1/3 and 1/1 methanol/ethyl acetate fractions are combined and concentrated to give the title compound as a foamy solid. NMR (CDCl3, 300 MHz) 7.64, 7.55, 7.24, 4.70, 4.10, 3.87, 3.12, 3.01, 2.57 and 1.36 δ; CMR (CDCl3, 75.47 MHz) 13.60, 14.77, 38.46, 44.80, 48.61, 73.57, 109.06, 109.17, 114.63, 131.64, 132.86, 142.52, 152.02 and 155.09 δ.

Workup

  1. filtrationThe mixture is then filtered
  2. concentrationthe filtrate concentrated
  3. customto give the crude product as a solid in an oil
  4. washeluted with ethyl acetate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-125b0bb01295445fa294ae1aa9ea141b
Source dataset
uspto-grants-1993_01
Patent number
US05182403

Reaction notes

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