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 2244384노트

반응식

HRID 2244384 반응식
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]

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-c635393286bc46b2ae838c61d834da4d
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07678818B2

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