Triethylamine → HCID 178454120, Verbindung

HRID 707231Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 707231
Cl.[Cl:2][C:3]1[C:8]([C:9]([CH3:14])([CH3:13])[C:10]([OH:12])=O)=[CH:7][CH:6]=[CH:5][N:4]=1.[C:15]([O:19][C:20](=[O:27])[NH:21][C@H:22]1[CH2:25][C@H:24]([NH2:26])[CH2:23]1)([CH3:18])([CH3:17])[CH3:16].C(N(CC)CC)C>ClCCl.O>[C:15]([O:19][C:20](=[O:27])[NH:21][C@H:22]1[CH2:25][C@H:24]([NH:26][C:10](=[O:12])[C:9]([C:8]2[C:3]([Cl:2])=[N:4][CH:5]=[CH:6][CH:7]=2)([CH3:14])[CH3:13])[CH2:23]1)([CH3:18])([CH3:16])[CH3:17]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 866941742-(2-Chloropyridin-3-yl)-2-methylpropanoic acid hydrochloride2×HCID 178454111HCID 178454111, Verbindung

Produkt 1

HCID 178454120HCID 178454120, VerbindungAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-(2-Chloropyridin-3-yl)-2-methylpropanoic acid hydrochloride (intermediate 25, 992 mg, 4.20 mmol), tert-butyl(trans-3-aminocyclobutyl)carbamate (939 mg, 5.04 mmol), hatu (2077 mg, 5.46 mmol) and triethylamine (2.4 ml, 16.81 mmol) were dissolved in dichloromethane (8.4 mL). The reaction mixture was stirred at room temperature for 21 hours then diluted with water and extracted with dichloromethane. The organic was washed with saturated ammonium chloride and dried over magnesium sulfate. Evaporation under reduced pressure and purification using silica chromatography (0% to 100% ethyl acetate in hexane gradient) gave tert-butyl(trans-3-(2-(2-chloropyridin-3-yl)-2-methylpropanamido)cyclobutyl)carbamate (1327 mg, 3.61 mmol, 86% yield) as white solid.

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. washThe organic was washed with saturated ammonium chloride
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation
  5. customunder reduced pressure and purification

Quellen und Nachweise

ORD-Eintrag
ord-33130e38549f447d9d93eaa5b4580931
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174992B2

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