HCID 22344717, compound → HCID 11508581, compound

HRID 583939Notes

Reaction equation

HRID 583939 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([S:9]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([N+:20]([O-])=O)[CH:13]=2)=[O:10])[CH:6]=[C:5]([O:23][CH3:24])[C:4]=1[O:25][CH3:26]>C(O)C.[Pd]>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][S:9]([C:7]2[CH:6]=[C:5]([O:23][CH3:24])[C:4]([O:25][CH3:26])=[C:3]([O:2][CH3:1])[CH:8]=2)=[O:10])=[CH:13][C:14]=1[NH2:20]

Participants

4

Reactant 1

HCID 22344717HCID 22344717, compound

Product 1

HCID 11508581HCID 11508581, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A room temperature solution of Example 90A (75 mg, 0.20 mmol) in ethanol (5 mL) was treated with 10% Pd/C (10 mg), stirred under a hydrogen atmosphere for 3 hours, heated to reflux, stirred for 3 hours, cooled to room temperature, filtered through diatomaceous earth (Celite®), and concentrated. The concentrate was purified by flash column chromatography with 50% ethyl acetate/dichloromethane to provide the desired product.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. stirringstirred for 3 hours
  4. filtrationfiltered through diatomaceous earth (Celite®)
  5. concentrationconcentrated
  6. customThe concentrate was purified by flash column chromatography with 50% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-667a493bee5345e8a2b48ce60542803a
Source dataset
uspto-grants-2005_08
Patent number
US06924304B2

Reaction notes

Loading…