Triethylamine → 3-(N,N-diethylamino) propionic acid, 2,3-diethyl-4-methoxynaphth-1-yl ester

HRID 649046Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 649046
C([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.[CH2:8]([C:10]1[C:19]([CH2:20][CH3:21])=[C:18]([O:22][CH3:23])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1O)[CH3:9].Cl.CN([CH:29]([CH3:33])[C:30]([OH:32])=[O:31])C.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH2:6]([N:3]([CH2:33][CH2:29][C:30]([O:32][C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]([O:22][CH3:23])=[C:19]([CH2:20][CH3:21])[C:10]=1[CH2:8][CH3:9])=[O:31])[CH2:4][CH3:5])[CH3:7]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 126649942,3-Diethyl-4-methoxynaphtholHCID 216146742-Dimethylamino-propionic acid hydrochloride

Produkt 1

HCID 571098023-(N,N-diethylamino) propionic acid, 2,3-diethyl-4-methoxynaphth-1-yl esterAusbeute 51,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Dry methylene chloride (30 ml) and triethylamine (0.33 ml, 2.34 mmole) are added to a mixture of 2,3-diethyl-4-methoxynaphthol (180 mg, 0.78 mmole), dimethylamino propionic acid hydrochloride (2 eq, 283 mg, 1.56 mmole), dicyclohexylcarbodiimide (2 eq, 322 mg, 1.56 mmole) and 4-dimethylaminpyridine (1 eq, 95 mg, 0.78 mmole) at room temperature under argon, and the resulting suspension is stirred at room temperature under argon for two days. The white precipitate is removed by filtration, and the filtrate is concentrated. Thick layer chromatography (silica gel, 2000 micron) developed by a 9:1 mixture of ether and n-hexane isolates 144 mg (51.8% ) of 3-(N,N-diethylamino) propionic acid, 2,3-diethyl-4-methoxynaphth-1-yl ester as a colorless oil.

Aufarbeitung

  1. customThe white precipitate is removed by filtration
  2. concentrationthe filtrate is concentrated
  3. additionThick layer chromatography (silica gel, 2000 micron) developed by a 9:1 mixture of ether and n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-eb61534544b34bdfb5b61227506f5515
Quelldatensatz
uspto-grants-1988_04
Patentnummer
US04737519

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