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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67483251, Verbindung

HRID 1884272
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1884272
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:36])[CH2:12][CH:13]([C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=2)[C:14]([C:16]2[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=2)=[O:15])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.[CH3:59][O:60][C:61](=[O:65])[CH2:62][CH2:63][NH2:64].CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:59][O:60][C:61](=[O:65])[CH2:62][CH2:63][NH:64][C:20](=[O:21])[C:19]1[CH:23]=[CH:24][C:16]([C:14](=[O:15])[CH:13]([C:25]2[CH:26]=[CH:27][C:28]([O:31][C:32]([F:33])([F:35])[F:34])=[CH:29][CH:30]=2)[CH2:12][C:11]([C:8]2[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=2)=[O:36])=[CH:17][CH:18]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 23508809HCID 23508809, Verbindung

Produkt 1

HCID 67483251
HCID 67483251, Verbindung
Ausbeute 104,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

4-[4-(4-tert-Butylphenyl)-4-oxo-2-(4-trifluoromethoxyphenyl)butyryl]benzoic acid (10.4 g, 20.86 mmol) was dissolved in DMF (150 mL) and added EDAC (5.60 g, 29.20) and HOBt (4.23 g, 31.29 mmol). After ½ h a solution of beta-alanine methyl ester hydrochloride (4.37 g, 31.29 mmol) and DIPEA (5.36 mL, 31.29 mmol) in DMF (20 mL) was added to the above mixture and the reaction mixture was stirred night over. The reaction was concentrated to approximately 100 mL and diluted with water (200 mL) and extracted with ethyl acetate (200 mL). The water phase was extracted with additional ethyl acetate (75 mL). The combined organic phases were washed with hydrochloric acid (0.2 N, 3×150 mL), aqueous sodium chloride (50% saturation, 3×150 mL) and dried over magnesium sulphate. The dried organic phase was filtered and evaporated to dryness to afford 3-{4-[4-(4-tert-butylphenyl)-4-oxo-2-(4-trifluoromethoxyphenyl)butyryl]benzoylamino}propionic acid methyl ester (12.76 g).

Aufarbeitung

  1. concentrationThe reaction was concentrated to approximately 100 mL
  2. additiondiluted with water (200 mL)
  3. extractionextracted with ethyl acetate (200 mL)
  4. extractionThe water phase was extracted with additional ethyl acetate (75 mL)
  5. washThe combined organic phases were washed with hydrochloric acid (0.2 N, 3×150 mL), aqueous sodium chloride (50% saturation, 3×150 mL)
  6. dry with materialdried over magnesium sulphate
  7. filtrationThe dried organic phase was filtered
  8. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-882567ca56c64f69bfb9b8373d25af9f
Quelldatensatz
uspto-grants-2004_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06762318B2

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