Ethanol → HCID 19045724, compound

HRID 1781512Notes

Reaction equation

HRID 1781512 reaction equation
C(OC(N([CH2:13][C:14]([NH:16][C:17]1([C:31](OCC)=[O:32])[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][C:21]([O:29][CH3:30])=[C:22]([O:27][CH3:28])[CH:23]=2)[CH2:18]1)=[O:15])C)=O)C1C=CC=CC=1.[CH2:36](O)[CH3:37]>[Pd].[C]>[CH3:28][O:27][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][C:21]=1[O:29][CH3:30])[CH2:18][C:17]1([C:31](=[O:32])[CH:36]([CH3:37])[CH2:13][C:14](=[O:15])[NH:16]1)[CH2:26][CH2:25]2

Participants

4

Reactant 2

HCID 702EthanolHCID 19045638HCID 19045638, compound

Product 1

HCID 19045724HCID 19045724, compound

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

A solution of ethyl 2-[(N-benzyloxycarbonyl-N-methylamino)acetylamino]-1,2,3,4-tetrahydro-6,7-dimethoxynaphthalene-2-carboxylate (550 mg, 1.1 mmol) in ethanol (20 ml) was hydrogenated in the presence of 10% Pd-carbon (250 mg) for 6 hr. The catalyst was filtered off and the filtrate was concentrated in vacuo. The residue was dissolved in 1N sodium hydroxide (2 ml) and THF (10 ml) and heated at 80° C. for 17 hr. The reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate. The solution was washed with water, and sat. sodium chloride, dried, and concentrated in vacuo. The residue was recrystallized from chloroform-isopropylether to give the titled compound (150 mg).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe residue was dissolved in 1N sodium hydroxide (2 ml)
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washThe solution was washed with water, and sat. sodium chloride
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customThe residue was recrystallized from chloroform-isopropylether

Sources & evidence

ORD record
ord-9bd1f43edb1547daa2f9d118ae4fcc96
Source dataset
uspto-grants-1997_05
Patent number
US05633248

Reaction notes

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