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4-Cyanobenzoic acid → N-[(1R)-2-(3-cyanophenoxy)-1-(4-iodobenzyl)ethyl]-4-cyanobenzamide

HRID 747736
ノート
印刷プレビュー

反応式

HRID 747736 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][CH:27]=1)[O:6][CH2:7][C@H:8]([NH:17][C:18](=[O:24])OC(C)(C)C)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([I:16])=[CH:12][CH:11]=1)#[N:2].[C:28]([C:30]1[CH:38]=[CH:37][C:33](C(O)=O)=[CH:32][CH:31]=1)#[N:29].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>Cl.O1CCOCC1.O1CCOCC1.O.C(N(CC)CC)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][CH:27]=1)[O:6][CH2:7][C@H:8]([NH:17][C:18](=[O:24])[C:33]1[CH:37]=[CH:38][C:30]([C:28]#[N:29])=[CH:31][CH:32]=1)[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([I:16])=[CH:14][CH:15]=1)#[N:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 120874-Cyanobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86760710t-butyl [(1R)-2-(3-cyanophenoxy)-1-(4-iodobenzyl)ethyl]carbamate

生成物 1

HCID 68831582N-[(1R)-2-(3-cyanophenoxy)-1-(4-iodobenzyl)ethyl]-4-cyanobenzamide

試薬・触媒・溶媒 4

HCID 962Water溶媒
HCID 8471Triethylamine溶媒
HCID 312751,4-Dioxane溶媒
HCID 204431481,4-Dioxane hydrochloride溶媒

実験手順

1.44 g (3.01 mmol) of t-butyl [(1R)-2-(3-cyanophenoxy)-1-(4-iodobenzyl)ethyl]carbamate was dissolved in 5 ml of 4 N dioxane hydrochloride and 2.5 ml of dioxane, and the solution was stirred for 15 hours. The solvent was evaporated under reduced pressure, and the residue was dissolved in 10 ml of dichloromethane. 488 mg (3.3 mmol) of 4-cyanobenzoic acid 1.3 ml (9.3 mmol) of triethylamine, 633 mg (1.5 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 445 mg (3.3 mmol) of 1-hydroxybenzotriazole were added to the solution, and they were stirred for 16 hours. The reaction liquid was diluted with water. After the extraction with ethyl acetate, the organic layer was successively washed with water, 1 N sodium hydroxide and saturated aqueous NaCl solution, and then dried over anhydrous magnesium sulfate. The solvent was evaporated. The residue was purified by the silica gel column chromatography to obtain the title compound.

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in 10 ml of dichloromethane
  3. customThe reaction liquid
  4. extractionAfter the extraction with ethyl acetate
  5. washthe organic layer was successively washed with water, 1 N sodium hydroxide and saturated aqueous NaCl solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customThe residue was purified by the silica gel column chromatography

出典と根拠

ORDレコード
ord-74825b9d5ea34663a00c65a2a17597a7
出典データセット
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07396844B1

反応ノート

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