Ethyl chloroformate → (S)-N-(alpha-ethylbenzyl)-3-(ethoxycarbonyloxy)-2-phenylquinoline-4-carboxamide

HRID 651061

Reaktionsgleichung

Reaktionsgleichung von HRID 651061
[CH2:1]([C@H:3]([NH:10][C:11]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:14]=1[OH:29])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].Cl[C:31]([O:33][CH2:34][CH3:35])=[O:32]>N1C=CC=CC=1>[CH2:1]([C@H:3]([NH:10][C:11]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:14]=1[O:29][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH3:2]

Komponenten

4

Edukt 2

HCID 10928Ethyl chloroformate2×HCID 5311424Talnetant

Produkt 1

HCID 54290349(S)-N-(alpha-ethylbenzyl)-3-(ethoxycarbonyloxy)-2-phenylquinoline-4-carboxamideAusbeute 42,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

0.5 g (1.3 mmol) of (S)-N-(α-ethylbenzyl)-3-hydroxy-2-phenylquinoline-4-carboxamide (compound of Description 1) were dissolved in 10 ml of pyridine; 0.5 ml (5.2 mmol) of ethyl chloroformate were added dropwise and the solution was refluxed under magnetical stirring for 8 hours. The reaction mixture was allowed to reach room temperature and left overnight. 1.0 ml (10.4 mmol) of ethyl chloroformate were added and the solution refluxed for 4 hours. The pyridine was evaporated off with toluene; the residue was dissolved in CH2Cl2, washed with H2O and the organic layer dried over na2SO4 and evaporated in-vacuo to dryness. The crude product was triturated with warm i-Pr2O to yield 0.25 g of the title compound as a yellow solid.

Aufarbeitung

  1. temperaturethe solution was refluxed
  2. customto reach room temperature
  3. waitleft overnight
  4. temperaturethe solution refluxed for 4 hours
  5. customThe pyridine was evaporated off with toluene
  6. dissolutionthe residue was dissolved in CH2Cl2
  7. washwashed with H2O
  8. customthe organic layer dried over na2SO4
  9. customevaporated in-vacuo to dryness
  10. customThe crude product was triturated with warm i-Pr2O

Quellen und Nachweise

ORD-Eintrag
ord-090dcc3f31c04bdca941b94b57ae12c8
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06277862B1

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