2,5-Dimethyl-3-furoyl Chloride → (S)-2,5-Dimethyl-furan-3-carboxylic acid (1-{4-[3-(4-ethoxy-phenoxy)-azetidin-1-yl]-phenyl}-ethyl)-amide

HRID 40513

Reaktionsgleichung

Reaktionsgleichung von HRID 40513
[CH3:1][C:2]1[O:3][C:4]([CH3:10])=[CH:5][C:6]=1[C:7](Cl)=[O:8].[CH2:11]([O:13][C:14]1[CH:33]=[CH:32][C:17]([O:18][CH:19]2[CH2:22][N:21]([C:23]3[CH:28]=[CH:27][C:26]([C@@H:29]([NH2:31])[CH3:30])=[CH:25][CH:24]=3)[CH2:20]2)=[CH:16][CH:15]=1)[CH3:12]>C(Cl)Cl>[CH2:11]([O:13][C:14]1[CH:33]=[CH:32][C:17]([O:18][CH:19]2[CH2:20][N:21]([C:23]3[CH:28]=[CH:27][C:26]([C@@H:29]([NH:31][C:7]([C:6]4[CH:5]=[C:4]([CH3:10])[O:3][C:2]=4[CH3:1])=[O:8])[CH3:30])=[CH:25][CH:24]=3)[CH2:22]2)=[CH:16][CH:15]=1)[CH3:12]

Komponenten

4

Edukt 2

HCID 27348042,5-Dimethyl-3-furoyl ChlorideHCID 86689010(S)-1-{4-[3-(4-Ethoxy-phenoxy)-azetidin-1-yl]-phenyl}-ethylamine

Produkt 1

HCID 71616304(S)-2,5-Dimethyl-furan-3-carboxylic acid (1-{4-[3-(4-ethoxy-phenoxy)-azetidin-1-yl]-phenyl}-ethyl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To 0.015 g (0.10 mmol) 2,5-dimethyl-furan-3-carbonyl chloride in 1 mL DCM is added a mixture of 0.031 g (0.10 mmol) (S)-1-{4-[3-(4-ethoxy-phenoxy)-azetidin-1-yl]-phenyl}-ethylamine (X.1) and 0.010 g (0.10 mmol) TEA in 0.5 mL DCM. The mixture is stirred for 12 h at rt. The solvent is removed in vacuo and the residue is purified by HPLC to yield the desired product.

Aufarbeitung

  1. customThe solvent is removed in vacuo
  2. customthe residue is purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-420d1ab6b86e45b88eef6d32ecab79ba
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530461B2

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