1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178500677, Verbindung

HRID 632935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 632935
[CH3:1][O:2][C:3](=[O:18])[CH2:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.CCN=C=NCCCN(C)C.[C:30]1([C:36]2[O:37][C:38]([C:49]([F:52])([F:51])[F:50])=[C:39]([C:41]([NH:43][CH2:44][CH2:45][C:46](O)=[O:47])=[O:42])[N:40]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)C(C)C)C>ClCCl.C([O-])(O)=O.[Na+]>[CH3:1][O:2][C:3](=[O:18])[CH2:4][C@H:5]1[CH2:6][CH2:7][C@H:8]([C:11]2[CH:12]=[CH:13][C:14]([NH:17][C:46](=[O:47])[CH2:45][CH2:44][NH:43][C:41]([C:39]3[N:40]=[C:36]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[O:37][C:38]=3[C:49]([F:51])([F:52])[F:50])=[O:42])=[CH:15][CH:16]=2)[CH2:9][CH2:10]1

Komponenten

8

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1179201883-[(2-Phenyl-5-trifluoromethyloxazole-4-carbonyl)amino]propionic acidHCID 178500653HCID 178500653, Verbindung

Produkt 1

HCID 178500677HCID 178500677, VerbindungAusbeute 98,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

Trans-[4-(4-aminophenyl)cyclohexyl]acetic acid methyl ester (150 mg, 0.6 mmol), EDCI (290.7 mg, 1.5 mmol), 3-[(2-phenyl-5-trifluoromethyloxazole-4-carbonyl)amino]propionic acid (228.9 mg, 0.7 mmol), HOBt (123 mg, 0.91 mmol) and ethyldiisopropylamine (275 mg, 0.21 mmol) dissolved in dichloromethane (15 mL) were stirred for 24 hours. The reaction mixture was diluted with aqueous NaHCO3 and extracted with dichloromethane. The extract was washed with brine and dried with anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by silica gel column chromatography to obtain the desired compound (330 mg, 98%) as a white solid.

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. washThe extract was washed with brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-16c12df558834f9b9e09570854efdfa3
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321728B2

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