Cesium fluoride → HCID 68543518、化合物

HRID 30776ノート

反応式

HRID 30776 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH:29]=[CH:28][C:12]([O:13][CH2:14][CH2:15][NH:16][C@@H:17]([CH3:27])[C@@H:18]([C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=3)[OH:19])=[CH:11][CH:10]=2)O1.Br[C:32]1[CH:40]=[CH:39][C:35]([C:36]([OH:38])=[O:37])=[CH:34][C:33]=1[CH2:41][CH3:42].[F-].[Cs+].O1CCOCC1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(O)C>[CH2:41]([C:33]1[CH:34]=[C:35]([C:36]([OH:38])=[O:37])[CH:39]=[CH:40][C:32]=1[C:9]1[CH:10]=[CH:11][C:12]([O:13][CH2:14][CH2:15][NH:16][C@@H:17]([CH3:27])[C@H:18]([OH:19])[C:20]2[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=2)=[CH:28][CH:29]=1)[CH3:42]

参加物

8

反応物 4

HCID 25953Cesium fluorideHCID 312751,4-DioxaneHCID 230907294-Bromo-3-ethylbenzoic acidHCID 685450254-((1R,2S)-2-(2-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]ethylamino}-1-hydroxypropyl)phenol

生成物 1

HCID 68543518HCID 68543518、化合物収率 23.7%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
140 °C

実験手順

A mixture of 4-((1R,2S)-2-{2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]ethylamino}-1-hydroxypropyl)phenol (0.04 g), 4-bromo-3-ethylbenzoic acid (0.044 g), tetrakis(triphenylphosphine)palladium (0.011 g), cesium fluoride (0.088 g), 1,4-dioxane (0.6 mL), ethanol (0.12 mL) and water (0.2 mL) was stirred at 140° C. for 5 min in a sealed tube. After being cooled to room temperature, the reaction mixture was purified by SCX ion exchange column chromatography (2 g, preconditioning: tetrahydrofuran, washing solvent:tetrahydrofuran, eluent:2 mol/L ammonia in methanol), followed by reverse phase column chromatography (Shiseido Capcell Pak C18 ODS, 5 μm, 120 Å, 20×50 mm, linear gradient 0.1% aqueous formic acid/acetonitrile=90/10-60/40) to afford the title compound (0.010 g) as a white amorphous. The structure and physical data were shown in table 3.

後処理

  1. temperatureAfter being cooled to room temperature
  2. customthe reaction mixture was purified by SCX ion exchange column chromatography (2 g, preconditioning: tetrahydrofuran, washing solvent:tetrahydrofuran, eluent:2 mol/L ammonia in methanol)

出典と根拠

ORDレコード
ord-3b4921e1c8b54f71ab89045f4b1c68d9
出典データセット
uspto-grants-2008_09
特許番号
US07423185B2

反応ノート

読み込み中…