Azetidine → 1-(Azetidin-1-yl)-2-[4-(benzyloxy)-2-methylphenyl]ethanone

HRID 1850716Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1850716
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=O)=[C:11]([CH3:19])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:20]1[CH2:23][CH2:22][CH2:21]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[N:20]1([C:16](=[O:18])[CH2:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:10][C:11]=2[CH3:19])[CH2:23][CH2:22][CH2:21]1

Komponenten

6

Edukt 4

HCID 10422AzetidineHCID 81531DiisopropylethylamineHCID 3907176[4-(Benzyloxy)-2-methylphenyl]acetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 708190121-(Azetidin-1-yl)-2-[4-(benzyloxy)-2-methylphenyl]ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

[4-(benzyloxy)-2-methylphenyl]acetic acid (0.5 g, 1.951 mmol) was dissolved in DMF (1 ml) and azetidine (0.167 g, 2.93 mmol), DIEA (0.511 ml, 2.93 mmol), and HATU (1.484 g, 3.90 mmol) added. The mixture was stirred at RT for 1 hr. The reside was purified by column chromatography using a Biotage RP C18 cartridge (30 g) using a gradient eluant of 10-100% water:acetonitrile+0.05% formic acid. to afford the title compound. LC/MS (m/z): 296 (M+H)+.

Aufarbeitung

  1. customThe reside was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2f18708fd49d45a6b8d1805134b49318
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957062B2

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