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

HRID 1474666Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1474666
[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). Azetidine (0.167 g, 2.93 mmol), DIEA (0.511 ml, 2.93 mmol), and HATU (1.484 g, 3.90 mmol) were added and the mixture 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-9ba6c6a26a4346a396c72c1ff31bbb47
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09018224B2

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