Triethylamine → HCID 178441265, Verbindung

HRID 1888687Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1888687
CCN=C=NC[CH2:7][CH2:8][N:9]([CH3:11])C.Cl.[CH2:13]([C:17]1=[CH:18][N:19]([C:36]([CH3:39])([CH3:38])[CH3:37])[S:20]/[C:21]/1=[N:22]\[C:23]([C@:25]1([CH3:35])[CH2:29][CH2:28][C@H:27]([C:30]([OH:32])=O)[C:26]1([CH3:34])[CH3:33])=[O:24])[CH2:14][CH2:15][CH3:16].OC1C2N=NNC=2C=CC=1.Cl.N1CCC1.C(N(CC)CC)C>C(OCC)(=O)C.O.CN(C)C=O>[N:9]1([C:30]([C@H:27]2[CH2:28][CH2:29][C@@:25]([CH3:35])([C:23](/[N:22]=[C:21]3/[C:17]([CH2:13][CH2:14][CH2:15][CH3:16])=[CH:18][N:19]([C:36]([CH3:38])([CH3:37])[CH3:39])[S:20]/3)=[O:24])[C:26]2([CH3:33])[CH3:34])=[O:32])[CH2:8][CH2:7][CH2:11]1

Komponenten

9

Edukt 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12308726Azetidine hydrochlorideHCID 178418300HCID 178418300, VerbindungHCID 178441278HCID 178441278, Verbindung

Produkt 1

HCID 178441265HCID 178441265, VerbindungAusbeute 58,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Solid N-(3-dimethylaminopropyl)-n′-ethylcarbodiimide hydrochloride (EDC) (Aldrich, 216 mg, 1.12 mmol), the product from Example 173 (296 mg, 0.750 mmol), hydroxybenzotriazole (Aldrich, 152 mg, 1.12 mmol), azetidine hydrochloride (Aldrich, 105 mg, 1.12 mmol), triethylamine (Aldrich, 152 mg, 1.50 mmol) and anhydrous N,N-dimethylformamide (4 mL) were mixed together at room temperature. Water was added to quench and the mixture was extracted with dichloromethane. The extracts were dried over sodium sulfate and concentrated by rotary evaporator to give a brown oil. Flash chromatography (silica gel: 20-75% ethyl acetate in hexanes) afforded 189 mg (58%) of the title compound. 1H NMR (DMSO-d6) δ 0.50 (s, 3H), 0.90 (t, J=7.8 Hz, 3H), 1.22 (s, 3H), 1.23 (s, 3H), 1.23-1.35 (m, 4H), 1.37-1.46 (m, 1H), 1.56 (s, 9H), 1.56-1.67 (m, 2H), 1.90-2.03 (m, 1H), 2.08-2.22 (m, 2H), 2.71-2.76 (m, 2H), 2.77-2.83 (m, 1H), 3.73-3.81 (m, 1H), 3.82-3.91 (m, 1H), 4.06-4.14 (m, 1H), 4.18-4.26 (m, 1H), 8.50 (s, 1H). MS (ESI+) m/z 434 (M+H)+. Anal. calcd. for C24H39N3O2S: C, 66.47; H, 9.06; N, 9.69. Found: C, 66.60; H, 9.02; N, 9.47.

Aufarbeitung

  1. customto quench
  2. extractionthe mixture was extracted with dichloromethane
  3. dry with materialThe extracts were dried over sodium sulfate
  4. concentrationconcentrated by rotary evaporator
  5. customto give a brown oil

Quellen und Nachweise

ORD-Eintrag
ord-c999a571b3d54a32a6b4c64fe46af011
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501794B2

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