Isopropanol → (R)-1-(2-(2-methylthiazol-4-yl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide

HRID 1255072

反応式

HRID 1255072 の反応式
[C:1]1([CH:7]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:8]([O:10][C@@H:11]2[CH:16]3[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]3)[CH2:12]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:26][CH2:27][C:28]([C:30]1[N:31]=[C:32]([CH3:35])[S:33][CH:34]=1)=[O:29].CC(O)C>C(#N)C>[Br-:26].[CH3:35][C:32]1[S:33][CH:34]=[C:30]([C:28](=[O:29])[CH2:27][N+:13]23[CH2:14][CH2:15][CH:16]([CH2:17][CH2:18]2)[C@@H:11]([O:10][C:8](=[O:9])[C@@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:12]3)[N:31]=1

参加物

5

反応物 3

HCID 3776IsopropanolHCID 128711692-Bromo-1-(2-methylthiazol-4-yl)ethanoneHCID 46239457(R)-quinuclidin-3-yl 2-phenyl-2-(phenylamino)acetate

生成物 1

HCID 86643226(R)-1-(2-(2-methylthiazol-4-yl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide収率 35.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

(R)-Phenyl-phenylamino-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Diastereoisomer 1 of C2) (75.0 mg, 0.22 mmol) and 2-bromo-1-(2-methylthiazol-4-yl)ethanone (I228) (49.1 mg, 0.22 mmol) in acetonitrile (5 mL) is heated at 100° C. for 75 minutes under microwave irradiation (UPLC-MS monitoring: complete conversion). The solvent is removed and the resulting brown solid is tritured with iPr20/Et2O (1/1) and then with iPrOH to obtain the title compound as a grey powder (43.3 mg, 35% yield, bromide salt, single diastereoisomers).

後処理

  1. customThe solvent is removed

出典と根拠

ORDレコード
ord-4f8319dd9c00415fba23f8333aa186a6
出典データセット
uspto-grants-2013_06
特許番号
US08455646B2

関連ノート

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