Water → N-((1RS,2SR)-2-hydroxy-2-(3-phenoxyphenyl)-1-((4-(trifluoromethyl)phenyl)methyl)ethyl)-4-fluoro-1-naphthalenecarboxamide

HRID 1610460노트

반응식

HRID 1610460 반응식
[NH2:1][CH:2]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=1)[CH:3]([C:5]1[CH:10]=[CH:9][C:8](OC2C=CC=CC=2)=[CH:7][CH:6]=1)[OH:4].[F:29][C:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:33]([C:40]([OH:42])=O)=[CH:32][CH:31]=1.Cl.C(N=C=NCCCN(C)C)C.ON1[C:60]2[CH:61]=[CH:62][CH:63]=[CH:64][C:59]=2N=N1.[OH2:65]>C(#N)C>[OH:4][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:65][C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[CH:6]=1)[CH:2]([NH:1][C:40]([C:33]1[C:34]2[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:30]([F:29])=[CH:31][CH:32]=1)=[O:42])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:26])([F:28])[F:27])=[CH:21][CH:20]=1

참가 물질

7

반응물 5

HCID 962WaterHCID 684484-Fluoro-1-naphthoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22261609(1RS,2SR)-2-amino-1-(4-phenoxyphenyl)-3-(4-(trifluoromethyl)phenyl)-1-propanol

생성물 1

HCID 22262079N-((1RS,2SR)-2-hydroxy-2-(3-phenoxyphenyl)-1-((4-(trifluoromethyl)phenyl)methyl)ethyl)-4-fluoro-1-naphthalenecarboxamide수율 77%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of (1RS,2SR)-2-amino-1-(4-phenoxyphenyl)-3-(4-(trifluoromethyl)phenyl)-1-propanol (400 mg, 1.03 mmol) in acetonitrile (30 ml) were added 4-fluoronaphthalenecarboxylic acid (196 mg, 1.03 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (247 mg, 1.55 mmol) and 1-hydroxy-1H-benzotriazole (158 mg, 1.03 mmol), and the mixture was stirred overnight at room temperature. The reaction solution was diluted with water (100 ml) and extracted with ethyl acetate (100 ml×2). The extract was washed successively with 1N hydrochloric acid, 1N aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. Recrystallization of the residue from ethyl acetate-hexane gave the title compound (446 mg, 77%).

후처리

  1. extractionextracted with ethyl acetate (100 ml×2)
  2. washThe extract was washed successively with 1N hydrochloric acid, 1N aqueous sodium hydroxide solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customRecrystallization of the residue from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-9248ae2fe9f04abbb0a36939d61eb283
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06982348B2

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