HCID 69832881, compound → HCID 69832857, compound

HRID 370037Notes

Reaction equation

HRID 370037 reaction equation
C(OC([N:11]1[C:20]2[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=2)[C@H:14]([N:25]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:13][C@@H:12]1[CH3:38])=O)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[CH2:29]([O:28][C:26](=[O:27])[N:25]([CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C@H:14]1[C:15]2[C:20](=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=2)[NH:11][C@@H:12]([CH3:38])[CH2:13]1)[CH3:30]

Participants

5

Reactant 2

HCID 69832881HCID 69832881, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69832857HCID 69832857, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of cis-4-(benzyl-ethoxycarbonyl-amino)-6,7-dimethoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid benzyl ester (Example 4) (1.0 g, 1.9 mmol) in ethanol (20 mL) was placed in a Parr bottle, charged with 10% palladium on carbon (100 mg), and agitated under 50 psi of hydrogen gas on a Parr shaker for 2 h. The mixture was then filtered through a bed of Celite®, eluting with ethyl acetate, and the filtrate concentrated in vacuo . The residue was purified by silica gel chromatography using 30% ethyl acetate/hexanes as eluent to afford 660 mg of the desired final product (89%): MS m/z 204 (M+ --PhCH2NHCO2Et--H2 +1); 1H NMR (CDCl3) δ 1.12 (d, 3H), 1.17 (t, 3H), 3.65 (s, 3H), 3.8 (s, 3H), 6.10 (C5, s, 1H), 6.44 (C8, s, 1H), 7.1-7.3 (m, 5H).

Workup

  1. filtrationThe mixture was then filtered through a bed of Celite®
  2. washeluting with ethyl acetate
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-e1976d98cc7c4917a6d17a6da61dc8ef
Source dataset
uspto-grants-2000_10
Patent number
US06140342

Reaction notes

Loading…