HCID 54319343, compound → HCID 53675954, compound

HRID 2288768Notes

Reaction equation

HRID 2288768 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:27]2[CH2:31][C@H:30]([CH2:32][NH:33][C:34](=[O:36])[CH3:35])[O:29][C:28]2=[O:37])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:15][C@@H:14]2[C@@H:10]([CH2:11][N:12]([C:16](=[O:26])[CH2:17][O:18]CC3C=CC=CC=3)[CH2:13]2)[CH2:9]1.[H][H]>[Pd].CO>[F:1][C:2]1[CH:3]=[C:4]([N:27]2[CH2:31][C@H:30]([CH2:32][NH:33][C:34](=[O:36])[CH3:35])[O:29][C:28]2=[O:37])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:15][C@@H:14]2[C@@H:10]([CH2:11][N:12]([C:16](=[O:26])[CH2:17][OH:18])[CH2:13]2)[CH2:9]1

Participants

5

Reactant 2

HCID 54319343HCID 54319343, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53675954HCID 53675954, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The (S)-N-[[3-[3-fluoro-4-[cis-3-(benzyloxyacetyl)-3,7-diazabicyclo[3.3.0]octan-7-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (110 mg, 0.22 mmol), methanol (25 mL) and 10% palladium on carbon (100 mg) are combined and placed under 40 p.s.i. of hydrogen and shaken for 5 days. The reaction is filtered through celite, concentrated in vacuo, and chromatographed on silica gel (230-400 mesh, 100 mL), eluting with chloroform/methanol (95/5). The appropriate fractions are combined (Rf =0.20, TLC, chloroform/methanol, 90/10) and concentrated in vacuo to give the title compound, mp 167-168° C.

Workup

  1. filtrationThe reaction is filtered through celite
  2. concentrationconcentrated in vacuo
  3. customchromatographed on silica gel (230-400 mesh, 100 mL)
  4. washeluting with chloroform/methanol (95/5)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3df5f271672b4c72a785655dc0eaeb5f
Source dataset
uspto-grants-2000_07
Patent number
US06090820

Reaction notes

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