2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → HCID 68350353, compound

HRID 625146Notes

Reaction equation

HRID 625146 reaction equation
[NH:1]([C:12]([O:14][CH2:15][CH:16]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13])[C@H:2]([C:4]([NH:6][C@H:7]([C:9](O)=[O:10])[CH3:8])=[O:5])[CH3:3].[NH2:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][OH:37])=[CH:32][CH:31]=1.CCOC1N(C(OCC)=O)C2C(=CC=CC=2)C=C1>C1COCC1.CC(O)C.C(OCC)(=O)C>[CH:18]1[C:17]2[CH:16]([CH2:15][O:14][C:12](=[O:13])[NH:1][C@H:2]([C:4](=[O:5])[NH:6][C@H:7]([C:9](=[O:10])[NH:29][C:30]3[CH:35]=[CH:34][C:33]([CH2:36][OH:37])=[CH:32][CH:31]=3)[CH3:8])[CH3:3])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]=2[CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 693314-Aminobenzyl alcoholHCID 7019063Fmoc-L-Ala-L-Ala-OH

Product 1

HCID 68350353HCID 68350353, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22055037Isopropanol ethyl acetateSolvent

Procedure

A solution of Fmoc-Ala-Ala-OH (1 g, 2.61 mmol, Eq: 1.00) and (4-aminophenyl)methanol (483 mg, 3.92 mmol, Eq: 1.5) in THF (20 ml) was treated with EEDQ (970 mg, 3.92 mmol, Eq: 1.5). The solution was stirred over night at room temperature. The mixture was diluted with 10% 2-propanol/ethyl acetate (100 mL) and the solution was washed with KHSO4 5%/K2SO4 10% (2×), water (1×) and brine (1×), dried over MgSO4 and evaporated in vacuo. The residue was sonicated in diethyl ether for several minutes and the solid was collected by filtration to obtain the product (1.27 g, 1.2 mmol) as light brown solid. MS (ISP): (M+H) 488.3

Workup

  1. washthe solution was washed with KHSO4 5%/K2SO4 10% (2×), water (1×) and brine (1×)
  2. dry with materialdried over MgSO4
  3. customevaporated in vacuo
  4. customThe residue was sonicated in diethyl ether for several minutes
  5. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-2a0863906e2c4a55a54ec49cf87322da
Source dataset
uspto-grants-2016_04
Patent number
US09301990B2

Reaction notes

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