Triethylamine → HCID 178522111, Verbindung

HRID 1846801Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1846801
[CH2:1]([O:8][CH:9]1[CH2:12][CH:11]([C:13]([OH:15])=[O:14])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1.C(N(CC)CC)C>CN(C=O)C.O>[CH2:1]([O:8][C@H:9]1[CH2:10][C@H:11]([C:13]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[O:15])[CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH2:1]([O:8][C@@H:9]1[CH2:12][C@H:11]([C:13]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[O:14])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 104392-AminopyridineHCID 128151113-(Benzyloxy)cyclobutane-1-carboxylic acid

Produkt 2

HCID 178522111HCID 178522111, VerbindungHCID 178522112HCID 178522112, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (2.21 g, 5.82 mmol) was added to a stirred mixture of 3-(benzyloxy)cyclobutanecarboxylic acid (0.80 g, 3.88 mmol), 2-aminopyridine (0.73 g, 7.76 mmol), and triethylamine (1.08 mL, 7.76 mmol) in DMF (15 mL). The reaction mixture was stirred at RT for 16 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic extract was separated, washed with saturated sodium chloride, dried over magnesium sulfate, filtered, and concentrated. The resulting crude product was purified via silica gel chromatography to give the separated diastereomers trans-3-(benzyloxy)-N-(pyridin-2-yl)cyclobutanecarboxamide and cis-3-(benzyloxy)-N-(pyridin-2-yl)cyclobutanecarboxamide.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. customwas separated
  4. washwashed with saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting crude product was purified via silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4e58d97c43f44b56ac04db04a48a0a60
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952037B2

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