Diisopropylethylamine → HCID 25242290、化合物

HRID 391228ノート

反応式

HRID 391228 の反応式
[CH2:1]([O:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=O)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH:19][C:20]12[CH2:29][CH:24]3[CH2:25][CH:26]([CH2:28][CH:22]([CH:23]3[NH:30][CH3:31])[CH2:21]1)[CH2:27]2.CCN(C(C)C)C(C)C>S(Cl)(Cl)=O.C(Cl)Cl.CN(C=O)C>[OH:19][C:20]12[CH2:29][CH:24]3[CH2:25][CH:26]([CH2:28][CH:22]([CH:23]3[N:30]([CH3:31])[C:13](=[O:15])[C:12]3[CH:16]=[CH:17][CH:18]=[C:10]([O:9][CH2:1][CH2:2][C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH:11]=3)[CH2:21]1)[CH2:27]2

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 37214804-(Methylamino)adamantan-1-olHCID 159431683-(2-Phenylethoxy)benzoic acid

生成物 1

HCID 25242290HCID 25242290、化合物収率 57.1%

試薬・触媒・溶媒 2

HCID 24386Thionyl Chloride溶媒HCID 22350042dichloromethane N,N-dimethylformamide溶媒

反応条件

温度
20 °C

実験手順

3-Phenethyloxy-benzoic acid (4.2 g, 17 mmol) was dissolved in thionylchloride (30 ml), and the mixture was stirred at 20° C. overnight. The solvent was removed, and 108 mg (0.41 mmol) of this acid chloride was added to a solution of 1-hydroxy-4-methylaminoadamantane (75 mg, 0.41 mmol) and DIPEA (0.14 ml, 0.83 mmol) in DCM/DMF (1:1, 4 ml). After stirring the reaction mixture at 20° C. overnight, the solution was concentrated in vacuo and purified by preparative LC-MS to give 95 mg of the title compound as a mixture of two isomers. 1H NMR (400 MHz, CDCl3): δ 7.21-7.36 (m, 6 H), 6.89-7.00 (m, 3 H), 4.10-4.23 (m, 3 H), 3.05-3.16 (m, 5 H), 2.54 (d, 2 H), 2.24 (d, 1 H), 1.49-2.04 (m, 11 H).

後処理

  1. customThe solvent was removed
  2. stirringAfter stirring the reaction mixture at 20° C. overnight
  3. concentrationthe solution was concentrated in vacuo
  4. custompurified by preparative LC-MS

出典と根拠

ORDレコード
ord-32fb56c1ab4f473aa4da8c3acfec49b4
出典データセット
uspto-grants-2013_02
特許番号
US08383820B2

反応ノート

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