Triethylamine → 4-(2-Fluoro-benzyl)-1-[3-(4-fluoro-phenyl)-propionyl]-piperidine-4-carboxylic acid [2-(4-ethyl-phenyl)-ethyl]-amide

HRID 730201Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 730201
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH2:28]([C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][NH:38][C:39]([C:41]2([CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=3[F:54])[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]2)=[O:40])=[CH:32][CH:31]=1)[CH3:29].[F:55][C:56]1[CH:61]=[CH:60][C:59]([CH2:62][CH2:63][C:64](O)=[O:65])=[CH:58][CH:57]=1.C(N(CC)CC)C>O1CCCC1.C(OCC)C>[CH2:28]([C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][NH:38][C:39]([C:41]2([CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=3[F:54])[CH2:42][CH2:43][N:44]([C:64](=[O:65])[CH2:63][CH2:62][C:59]3[CH:60]=[CH:61][C:56]([F:55])=[CH:57][CH:58]=3)[CH2:45][CH2:46]2)=[O:40])=[CH:32][CH:31]=1)[CH3:29]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 1363023-(4-Fluorophenyl)propionic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 236009334-(2-Fluoro-benzyl)-piperidine-4-carboxylic acid [2-(4-ethyl-phenyl)-ethyl]-amide

Produkt 1

HCID 236009324-(2-Fluoro-benzyl)-1-[3-(4-fluoro-phenyl)-propionyl]-piperidine-4-carboxylic acid [2-(4-ethyl-phenyl)-ethyl]-amideAusbeute 40,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (0.266 g, 0.602 mmol) was added to a solution of 4-(2-fluoro-benzyl)-piperidine-4-carboxylic acid [2-(4-ethyl-phenyl)-ethyl]-amide (0.185 g, 0.502 mmol), 3-(4-fluoro-phenyl)-propionic acid (0.101 g, 0.602 mmol) and triethylamine (0.210 mL, 1.51 mmol) in tetrahydrofuran (5 mL). After 1 h the mixture was diluted with ethyl ether (20 mL), washed with saturated aqueous sodium bicarbonate (20 mL) followed by water (2×10 mL). The organic layer was collected, concentrated under reduced pressure and the crude product purified by column chromatography to give 0.105 g (40 %) of 4-(2-fluoro-benzyl)-1-[3-(4-fluoro-phenyl)-propionyl]-piperidine-4-carboxylic acid [2-(4-ethyl-phenyl)-ethyl]-amide LRMS m/z 519.2 (M+H)+.

Aufarbeitung

  1. washwashed with saturated aqueous sodium bicarbonate (20 mL)
  2. customThe organic layer was collected
  3. concentrationconcentrated under reduced pressure
  4. customthe crude product purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-288feefb00534232b9ebfdc1e9690cee
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582654B2

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