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

HRID 892271ノート

反応式

HRID 892271 の反応式
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]

参加物

7

反応物 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

生成物 1

HCID 236009324-(2-Fluoro-benzyl)-1-[3-(4-fluoro-phenyl)-propionyl]-piperidine-4-carboxylic acid [2-(4-ethyl-phenyl)-ethyl]-amide収率 40.3%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-9a01992f130d4ee99ca225187bfc70a9
出典データセット
uspto-grants-2006_02
特許番号
US07005436B2

反応ノート

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