Hydrogen Peroxide → 4-[4-(2-Benzylamino-ethyl)-phenoxy]-2-chloro-benzamide

HRID 130721ノート

反応式

HRID 130721 の反応式
C(OC(=O)[N:7]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[C:19]([Cl:25])[CH:18]=2)=[CH:12][CH:11]=1)(C)(C)C.OO.C([O-])([O-])=[O:37].[K+].[K+].FC(F)(F)C(O)=O>CS(C)=O.C(Cl)Cl>[CH2:26]([NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([NH2:24])=[O:37])=[C:19]([Cl:25])[CH:18]=2)=[CH:12][CH:11]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

参加物

7

反応物 4

HCID 784Hydrogen PeroxideHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 59729914Benzyl-{2-[4-(3-chloro-4-cyano-phenoxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester

生成物 1

HCID 597301314-[4-(2-Benzylamino-ethyl)-phenoxy]-2-chloro-benzamide収率 149.7%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 6344Dichloromethane溶媒

実験手順

Combine the compound of step 1 (95 mg, 0.21 mmol), H2O2 (25 μl) and K2CO3 (15 mg, 0.10 mmol) in DMSO (0.8 mL), and stir the mixture at room temperature overnight. Add water and extract the aqueous layer with EtOAc. Dry the organic layer over Na2SO4 and eliminate the solvent. Purify by flash chromatography (EtOAc/hexane 50/50) to give a yellow oil. Dissolve the oil in CH2Cl2 (3 mL) and add trifluoroacetic acid (240 μL), and stir the mixture at room temperature for 4 hour. Eliminate the solvent. Purify by an SCX column to give the title compound (57 mg, 76%). Electrospray MS M+1 ion=381. 1H-NMR (CDCl3, 400 MHz): 7.82 (d, 1H, J=8.5 Hz), 7.35-7.20 (m, 7H), 6.99-6.95 (m, 3H), 6.90 (dd, 1H, J=2.5 and 8.5 Hz), 6.53 (m, 2H), 3.83 (s, 2H), 2.95-2.89 (m, 2H), 2.86-2.81 (m, 2H).

後処理

  1. extractionAdd water and extract the aqueous layer with EtOAc
  2. dry with materialDry the organic layer over Na2SO4
  3. customPurify by flash chromatography (EtOAc/hexane 50/50)
  4. customto give a yellow oil
  5. customPurify by an SCX column

出典と根拠

ORDレコード
ord-41553e654d674f76847ae2a4c8e77b02
出典データセット
uspto-grants-2008_06
特許番号
US07381719B2

反応ノート

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