N-(2-Methoxyethyl)ethylamine → HCID 178464021, Verbindung

HRID 25636

Reaktionsgleichung

Reaktionsgleichung von HRID 25636
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][C:7]([N:9]([CH3:24])[C@H:10]2[CH2:15][CH2:14][C@H:13]([C:16]#[C:17][CH2:18]OS(C)(=O)=O)[CH2:12][CH2:11]2)=[O:8])=[CH:4][CH:3]=1.[CH2:27]([NH:29][CH2:30][CH2:31][O:32][CH3:33])[CH3:28]>CO>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][C:7](=[O:8])[N:9]([C@H:10]2[CH2:15][CH2:14][C@H:13]([C:16]#[C:17][CH2:18][N:29]([CH2:27][CH3:28])[CH2:30][CH2:31][O:32][CH3:33])[CH2:12][CH2:11]2)[CH3:24])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 546877N-(2-Methoxyethyl)ethylamineHCID 178485964HCID 178485964, Verbindung

Produkt 1

HCID 178464021HCID 178464021, VerbindungAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 200 mg (corresponds to 0.43 mmol) of trans-Methanesulfonic acid 3-{4-[(4-chloro-phenoxycarbonyl)-methyl-amino]-cyclohexyl}-prop-2-ynyl ester in 4.3 ml of methanol was cooled to 0° C., treated with 0.44 ml (1 mmol) of Ethyl-(2-methoxy-ethyl)-amine and stirred over night at RT. The solvent was evaporated and the residue extracted with aqueous saturated NaHCO3/Et2O (3×). The organic phase was dried with Na2SO4, filtered and evaporated. Purification by flash column chromatography on silica gel (CH2Cl2/MeOH 99:1) gave 144 mg (83%) of pure trans-(4-{3-[Ethyl-(2-methoxy-ethyl)-amino]-prop-1-ynyl}-cyclohexyl)-methyl-carbamic acid 4-chloro-phenyl ester, MS: 407 (MH+, 1Cl). The following compounds were prepared from the corresponding mesylates and secondary amines:

Aufarbeitung

  1. customThe solvent was evaporated
  2. extractionthe residue extracted with aqueous saturated NaHCO3/Et2O (3×)
  3. dry with materialThe organic phase was dried with Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash column chromatography on silica gel (CH2Cl2/MeOH 99:1)

Quellen und Nachweise

ORD-Eintrag
ord-edb488e4a25f4f5bb16d32bd7b37e45c
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858651B2

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