Ethyl Acetate → HCID 21698569, compound

HRID 379350Notes

Reaction equation

HRID 379350 reaction equation
[CH2:1]([C:3]1([CH3:24])[CH2:8][C:7]([CH3:10])([CH3:9])[CH2:6][CH:5]([NH:11][C:12](=[O:23])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[C:14]=2[OH:22])[CH2:4]1)[CH3:2].[H][H].[C:27](OCC)(=[O:29])C>[Pd]>[CH:27]([NH:19][C:15]1[C:14]([OH:22])=[C:13]([CH:18]=[CH:17][CH:16]=1)[C:12]([NH:11][CH:5]1[CH2:6][C:7]([CH3:10])([CH3:9])[CH2:8][C:3]([CH2:1][CH3:2])([CH3:24])[CH2:4]1)=[O:23])=[O:29]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21698574HCID 21698574, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 21698569HCID 21698569, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of N-(3-ethyl-3,5,5-trimethylcyclohexyl)-2-hydroxy-3-nitrobenzamide (3.60 g) in ethyl acetate (75 ml) was added 5% Pd/C (0.40 g) catalyst. The resulting mixture was subjected to a hydrogen atmosphere (initial H2 pressure=50 psi) using a Parr shaker apparatus. When hydrogen uptake ceased (approximately 30 minutes), the hydrogen atmosphere was purged. A stir bar was added to the reaction bottle and to the stirred reaction mixture acetic-formic anhydride (3 ml) was added all at once. After stirring at room temperature for 30 minutes, the reaction was filtered, washed with saturated sodium bicarbonate solution (100 ml). then with a saturated sodium chloride solution (100 ml), dried (MgSO4) and the solvent evaporated to give the desired product as a white solid foam (3.5 g). An analytical sample could be prepared by recrystallization from a methanol/water mixture to give an off-white crystalline solid (m.p.=166-168° C.). 13C NMR (CDCl3) showed this material to be approximately a 6:4 mixture of diastereomers.

Workup

  1. custom(approximately 30 minutes)
  2. customthe hydrogen atmosphere was purged
  3. additionA stir bar was added to the reaction bottle and to the stirred reaction mixture acetic-formic anhydride (3 ml)
  4. additionwas added all at once
  5. filtrationthe reaction was filtered
  6. washwashed with saturated sodium bicarbonate solution (100 ml)
  7. dry with materialthen with a saturated sodium chloride solution (100 ml), dried (MgSO4)
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-81b8de6077244d4bbfa485f9dfc5e9ae
Source dataset
uspto-grants-2001_10
Patent number
US06297401B1

Reaction notes

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