2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → HCID 13036549, compound

HRID 1903365Notes

Reaction equation

HRID 1903365 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])[CH3:3].Cl.[CH3:14][O:15][C:16](=[O:26])[C@H:17]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[NH2:18].C(OC(N1C2C(=CC=CC=2)C=CC1OCC)=O)C>C(Cl)Cl>[CH3:14][O:15][C:16](=[O:26])[C@H:17]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[NH:18][C:10](=[O:12])[CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7]

Participants

5

Reactant 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 78288N-(tert-butoxycarbonyl)glycine

Product 1

HCID 13036549HCID 13036549, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

t-Boc-glycine (1.75 g, 1.00 ×10-2 mole), L-phenylalanine methyl ester hydrochloride (2.16 g, 1.00 ×10-2 mole), and N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (2.47 g, 1.00 ×10-2 mole), and CH2Cl2 (50 ml) are stirred at room temperature for 16 hours. The reaction mixture is then washed in turn with 0.5M aqueous HCl (2 times) and saturated aqueous NaHCO3 before being dried over Na2SO4. Filtration of the drying agent and evaporation of the filtrate gives 6as an extremely viscous, almost colorless oil, which was shown to be homogeneous by TLC on silica gel plates and the structure corroborated by NMR. NMR (CDCl3) δ1.42 (S, 9, t-boc), 3.02 (d,2, benzylic methylene), 3.59 (S, 3, ester), 7.13 (S, 5, aromatic).

Workup

  1. washThe reaction mixture is then washed in turn with 0.5M aqueous HCl (2 times) and saturated aqueous NaHCO3
  2. dry with materialbefore being dried over Na2SO4
  3. filtrationFiltration of the drying agent and evaporation of the filtrate
  4. customgives 6as an extremely viscous, almost colorless oil, which

Sources & evidence

ORD record
ord-94dbf01a3b2b43a09e07a789da81e3ee
Source dataset
uspto-grants-1984_03
Patent number
US04435571

Reaction notes

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