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Triethylamine → (S)-N-[1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethyl]-2,3-diphenylpropanamide

HRID 335018
ノート
印刷プレビュー

反応式

HRID 335018 の反応式
Br.[CH2:2]([C:4]1[N:5]=[C:6]([C@@H:9]([NH2:20])[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[S:7][CH:8]=1)[CH3:3].[C:21]1([C:27]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)(C)[C:28]([OH:30])=O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.ON1C2C=CC=C[C:42]=2N=N1.CN(C)CCCN=C=NCC.C(N(CC)CC)C>CN(C=O)C.O>[CH2:2]([C:4]1[N:5]=[C:6]([CH:9]([NH:20][C:28](=[O:30])[C@H:27]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:21][C:26]2[CH:42]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[S:7][CH:8]=1)[CH3:3]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 796762,2-Diphenylpropionic acidHCID 666949351-(S)-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethyl amine hydrobromide

生成物 1

HCID 66695002
(S)-N-[1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethyl]-2,3-diphenylpropanamide
収率 70%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a solution of 1-(S)-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethyl amine hydrobromide, 3, (0.95 g, 2.65 mmol), diphenylpropionic acid (0.60 g, 2.65 mmol) and 1-hydroxybenzotriazole (HOBt) (0.180 g, 1.33 mmol) in DMF (10 mL) at 00, is added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDCI) (0.502 g, 2.62 mmol) followed by triethylamine (1.1 mL, 7.95 mmol). The mixture is stirred at 0° C. for 30 minutes then at room temperature overnight. The reaction mixture is diluted with water and extracted with EtOAc. The combined organic phase is washed with 1N aqueous HCl, 5% aqueous NaHCO3, water and brine, and dried over Na2SO4. The solvent is removed in vacuo to afford 0.903 g (70% yield) of the desired product which is used without further purification.

後処理

  1. customat room temperature
  2. customovernight
  3. extractionextracted with EtOAc
  4. washThe combined organic phase is washed with 1N aqueous HCl, 5% aqueous NaHCO3, water and brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent is removed in vacuo

出典と根拠

ORDレコード
ord-90fdf5fe4f174adcb0f997c5c9583625
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08883832B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート