HCID 14975959, compound → HCID 9993062, compound

HRID 1378742Notes

Reaction equation

HRID 1378742 reaction equation
C([O:3][C:4](=O)[CH2:5][N:6]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:7]1[C:12]([N+:13]([O-])=O)=[CH:11][CH:10]=[CH:9][C:8]=1[F:16])C>[Pd].CO>[C:20]([O:19][C:17]([N:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][C:8]=2[F:16])[NH:13][C:4](=[O:3])[CH2:5]1)=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 1

HCID 14975959HCID 14975959, compound

Product 1

HCID 9993062HCID 9993062, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2.06 g of N-(tert-butyloxycarbonyl)-N-(2-fluoro-6-nitrophenyl)glycine ethyl ester (XX, EXAMPLE 22, 2.06 g) and palladium on carbon (10%, 0.19 g) in methanol (150 ml) is shaken under hydrogen on a Parr apparatus at 37 psi for 1 hr. The catalyst is then filtered off and p-toluenesulfonic acid 0.016 g) is added. The solution is stirred at 80° for 1 hr and then at 20°-25° overnight The solvent is then removed under reduced pressure and the residue is chromatographed on silica gel (200 ml) eluting with ethyl acetate/dichloromethane (5/95). The appropriate fractions are pooled and concentrated to give the title compound, mp 155°-156°; MS (m/z) at 266; NMR (CDCl3) 1.48, 6.70, 6.84, 7.12 and 8.61 δ.

Workup

  1. filtrationThe catalyst is then filtered off
  2. additionp-toluenesulfonic acid 0.016 g) is added
  3. stirringThe solution is stirred at 80° for 1 hr
  4. customat 20°-25° overnight The solvent is then removed under reduced pressure
  5. customthe residue is chromatographed on silica gel (200 ml)
  6. washeluting with ethyl acetate/dichloromethane (5/95)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ff4c2dfc85064662aaf6d45d979882e7
Source dataset
uspto-grants-1997_09
Patent number
US05668282

Reaction notes

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