Diisopropylethylamine → (S)-1-Methyl-cyclobutanecarboxylic acid (1-{4-[3-(4-ethoxy-phenoxy)-azetidin-1-yl]-phenyl}-ethyl)-amide

HRID 40512

Reaktionsgleichung

Reaktionsgleichung von HRID 40512
[CH3:1][C:2]1([C:6]([OH:8])=O)[CH2:5][CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH2:40]([O:42][C:43]1[CH:62]=[CH:61][C:46]([O:47][CH:48]2[CH2:51][N:50]([C:52]3[CH:57]=[CH:56][C:55]([C@@H:58]([NH2:60])[CH3:59])=[CH:54][CH:53]=3)[CH2:49]2)=[CH:45][CH:44]=1)[CH3:41]>CN(C=O)C>[CH2:40]([O:42][C:43]1[CH:62]=[CH:61][C:46]([O:47][CH:48]2[CH2:49][N:50]([C:52]3[CH:57]=[CH:56][C:55]([C@@H:58]([NH:60][C:6]([C:2]4([CH3:1])[CH2:3][CH2:4][CH2:5]4)=[O:8])[CH3:59])=[CH:54][CH:53]=3)[CH2:51]2)=[CH:45][CH:44]=1)[CH3:41]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 127574881-Methylcyclobutane-1-carboxylic acidHCID 86689010(S)-1-{4-[3-(4-Ethoxy-phenoxy)-azetidin-1-yl]-phenyl}-ethylamine

Produkt 1

HCID 71616303(S)-1-Methyl-cyclobutanecarboxylic acid (1-{4-[3-(4-ethoxy-phenoxy)-azetidin-1-yl]-phenyl}-ethyl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To 0.011 g (0.10 mmol) 1-methyl-cyclobutanecarboxylic acid in 1 mL DMF are added 0.035 mL (0.20 mmol) DIPEA and 0.032 g (49.1 mmol) TBTU. The mixture is stirred for 15 min at rt. Subsequently 0.031 g (0.10 mmol) (S)-1-{4-[3-(4-ethoxy-phenoxy)-azetidin-1-yl]-phenyl}-ethylamine (X.1) are added and stirring is continued for 12 h at rt. The mixture is directly purified by HPLC to yield the desired product.

Aufarbeitung

  1. stirringstirring
  2. waitis continued for 12 h at rt
  3. customThe mixture is directly purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-2f7218bb3f9e4e3d8891d2c29fb9ec06
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530461B2

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