2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → Boc-Dap(Fmoc) N-palmityl-N-oleyl-amide

HRID 1050838Notes

Reaction equation

HRID 1050838 reaction equation
[CH2:1]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].CCOC1N(C(OCC)=O)C2C(=CC=CC=2)C=C1.[NH:54]([C:78]([O:80][C:81]([CH3:84])([CH3:83])[CH3:82])=[O:79])[C@H:55]([C:75]([OH:77])=[O:76])[CH2:56][NH:57][C:58]([O:60][CH2:61][CH:62]1[C:74]2[C:69](=[CH:70][CH:71]=[CH:72][CH:73]=2)[C:68]2[C:63]1=[CH:64][CH:65]=[CH:66][CH:67]=2)=[O:59].CCCCCC.C(OC(=O)C)C>ClCCl>[NH:54]([C:78]([O:80][C:81]([CH3:84])([CH3:83])[CH3:82])=[O:79])[C@H:55]([C:75]([OH:77])=[O:76])[CH2:56][NH:57][C:58]([O:60][CH2:61][CH:62]1[C:74]2[C:69](=[CH:70][CH:71]=[CH:72][CH:73]=2)[C:68]2[C:63]1=[CH:64][CH:65]=[CH:66][CH:67]=2)=[O:59].[CH2:20]([N-:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Participants

6

Reactant 4

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 7019527(2S)-2-(((tert-butoxy)carbonyl)amino)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)propanoic acidHCID 21226206Ethyl acetate hexaneHCID 86624385HCID 86624385, compound

Product 1

HCID 131729180Boc-Dap(Fmoc) N-palmityl-N-oleyl-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

521 mg (1.06 mmol)N-oleyl-palmitylamine in 10 ml anhydrous dichloromethane are dissolved in a 50 ml round-bottom flask and 289 mg (1.17 mmol) EEDQ are added. Subsequently, 500 mg (1.17 mmol) Boc-Dap(Fmoc)-OH are added under steering and the mixture is steered at room temperature for 20 hours. The solution is transferred with 80 ml dichloromethane into a separating funnel and washed three times with 20 ml 0.1 N HCl each and once with 20 ml saturated NaHCO3 solution. After drying over Na2SO4 the solvent is removed using a rotary evaporator (FIG. 4). A yellowish viscous oil is obtained which is not further purified. In thin layer chromatography using hexane/ethylacetate of 1:1 a Rf of 0.70 was observed.

Workup

  1. washwashed three times with 20 ml 0.1 N HCl each and once with 20 ml saturated NaHCO3 solution
  2. dry with materialAfter drying over Na2SO4 the solvent
  3. customis removed
  4. customa rotary evaporator (FIG. 4)
  5. customA yellowish viscous oil is obtained which

Sources & evidence

ORD record
ord-ad2e97acf0da48a49e8bebead2895170
Source dataset
uspto-grants-2016_07
Patent number
US09387262B2

Reaction notes

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