Dicyclohexylcarbodiimide → Ethyl 3-(3,4-dimethoxyphenyl)-2-{[4-(isopropyloxy)phenyl]carbonylamino}propionate

HRID 1986882

Reaktionsgleichung

Reaktionsgleichung von HRID 1986882
[NH2:1][CH:2]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH:19]([O:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][CH:24]=1)([CH3:21])[CH3:20].O.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH3:18][O:17][C:11]1[CH:10]=[C:9]([CH2:8][CH:2]([NH:1][C:27]([C:26]2[CH:30]=[CH:31][C:23]([O:22][CH:19]([CH3:21])[CH3:20])=[CH:24][CH:25]=2)=[O:28])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:14]=[CH:13][C:12]=1[O:15][CH3:16]

Komponenten

6

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 729724-Isopropoxybenzoic acidHCID 420232Ethyl 2-amino-3-(3,4-dimethoxyphenyl)propanoateHCID 27960291-Hydroxybenzotriazole hydrate

Produkt 1

HCID 68826043Ethyl 3-(3,4-dimethoxyphenyl)-2-{[4-(isopropyloxy)phenyl]carbonylamino}propionate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Ethyl 2-amino-3-(3,4-dimethoxyphenyl)propionate (the compound obtained in Example 1-(1)) (15.2 g), 4-isopropyloxybenzoic acid (10.8 g), and 1-hydroxybenzotriazole monohydrate (9.2 g) are dissolved in methylene chloride (120 ml), and thereto is added 1,3-dicyclohexylcarbodiimide (12.4 g) under ice-cooling, and the mixture is stirred at room temperature overnight. The insoluble materials are removed by filtration, and the filtrate is washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The precipitated crystals are collected by filtration with diethyl ether to give ethyl 3-(3,4-dimethoxyphenyl)-2-{[4-(isopropyloxy)-phenyl]carbonylamino}propionate (24.2 g).

Aufarbeitung

  1. temperaturecooling
  2. customThe insoluble materials are removed by filtration
  3. washthe filtrate is washed with a saturated aqueous sodium hydrogen carbonate solution
  4. dry with materiala saturated brine, dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. filtrationThe precipitated crystals are collected by filtration with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-144aa40ed9d048fab83499a99dcf4895
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07550476B2

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