2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → (E)-ethyl 3-(4-(1-(tert-butoxycarbonylamino)cyclopentanecarboxamido)phenyl)acrylate

HRID 860712Notes

Reaction equation

HRID 860712 reaction equation
NC1(C(NC2C=CC(C=CC([O-])=O)=CC=2)=O)CCCC1.CCOC1N(C(OCC)=O)C2C(=CC=CC=2)C=C1.[NH2:39][C:40]1[CH:45]=[CH:44][C:43](/[CH:46]=[CH:47]/[C:48]([O:50][CH2:51][CH3:52])=[O:49])=[CH:42][CH:41]=1.[C:53]([O:57][C:58]([NH:60][C:61]1([C:66](O)=[O:67])[CH2:65][CH2:64][CH2:63][CH2:62]1)=[O:59])([CH3:56])([CH3:55])[CH3:54]>C1COCC1>[C:53]([O:57][C:58]([NH:60][C:61]1([C:66]([NH:39][C:40]2[CH:41]=[CH:42][C:43](/[CH:46]=[CH:47]/[C:48]([O:50][CH2:51][CH3:52])=[O:49])=[CH:44][CH:45]=2)=[O:67])[CH2:65][CH2:64][CH2:63][CH2:62]1)=[O:59])([CH3:56])([CH3:55])[CH3:54]

Participants

6

Reactant 4

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 736317Ethyl 4-aminocinnamateHCID 27346451-tert-Butoxycarbonylaminocyclopentanecarboxylic acidHCID 866035113-(4-(1-Aminocyclopentanecarboxamido)phenyl)acrylate

Product 1

HCID 59016322(E)-ethyl 3-(4-(1-(tert-butoxycarbonylamino)cyclopentanecarboxamido)phenyl)acrylateYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(E)-ethyl (3-(4-(1-aminocyclopentanecarboxamido)phenyl)acrylate. EEDQ (593 mg, 2.4 mmol) was added to a solution of (E)-ethyl 3-(4-aminophenyl)acrylate (417 mg, 2.18 mmol) and 1-(tert-butoxycarbonylamino)cyclopentanecarboxylic acid (500 mg, 2.18 mmol) in THF (6 mL). The solution was stirred at reflux for 3–4 hours. The mixture was concentrated and the residue partitioned between dichloromethane and water. The organic layer was washed sequentially with dilute HCl, water, and brine. The solution was dried over Na2SO4 and filtered. Dilution of the filtrate with hexanes resulted in the crystallization of (E)-ethyl 3-(4-(1-(tert-butoxycarbonylamino)cyclopentanecarboxamido)phenyl)acrylate as a pale yellow solid (360 mg, 37% yield). ESI-MS m/z 403 (MH+).

Workup

  1. temperatureat reflux for 3–4 hours
  2. concentrationThe mixture was concentrated
  3. customthe residue partitioned between dichloromethane and water
  4. washThe organic layer was washed sequentially with dilute HCl, water, and brine
  5. dry with materialThe solution was dried over Na2SO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-91ff1d50d0574589a06aeaa885f350ed
Source dataset
uspto-grants-2006_12
Patent number
US07153848B2

Reaction notes

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