N-(4-benzyloxy-benzyl)-5-chloro-2-methylamino-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide → 5-chloro-N-(4-hydroxy-benzyl)-2-methylamino-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide

HRID 2244384ノート

反応式

HRID 2244384 の反応式
C([O:8][C:9]1[CH:39]=[CH:38][C:12]([CH2:13][N:14]([CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=2)[C:15](=[O:25])[C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=2[NH:23][CH3:24])=[CH:11][CH:10]=1)C1C=CC=CC=1>C(OC(=O)C)C.[Pd]>[Cl:22][C:20]1[CH:19]=[CH:18][C:17]([NH:23][CH3:24])=[C:16]([CH:21]=1)[C:15]([N:14]([CH2:13][C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:39][CH:38]=1)[CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:35])[F:36])[CH:29]=1)=[O:25]

参加物

4

反応物 1

HCID 68696190N-(4-benzyloxy-benzyl)-5-chloro-2-methylamino-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide

生成物 1

HCID 687030505-chloro-N-(4-hydroxy-benzyl)-2-methylamino-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide収率 75%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 930 mg (1.68 mmol) of N-(4-benzyloxy-benzyl)-5-chloro-2-methylamino-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide (2 mmol) in 30 ml ethylacetate was hydrogenated over 300 mg of 5% Pd—C for 4 hours at RT. After completion of the reaction, the suspension was filtered, the catalyst washed with additional ethyl acetate and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (silica gel; heptane/-EtOAc 3:1) to give 339 mg 5-chloro-N-(4-hydroxy-benzyl)-2-methylamino-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide (75%) as a white foam. MS (ISP) 463 (M+H)+.

後処理

  1. customAfter completion of the reaction
  2. filtrationthe suspension was filtered
  3. washthe catalyst washed with additional ethyl acetate
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by column chromatography (silica gel; heptane/-EtOAc 3:1)

出典と根拠

ORDレコード
ord-c635393286bc46b2ae838c61d834da4d
出典データセット
uspto-grants-2010_03
特許番号
US07678818B2

反応ノート

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