Dicyclohexylcarbodiimide → 5-Bromo-2-(3-tert-butoxycarbonyl-propoxy)-4-chloro-benzoic acid 2-trimethylsilanyl-ethyl ester

HRID 1848639ノート

反応式

HRID 1848639 の反応式
[Br:1][C:2]1[C:3]([Cl:22])=[CH:4][C:5]([O:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH3:23][Si:24]([CH3:29])([CH3:28])[CH2:25][CH2:26]O.C1(N=C=NC2CCCCC2)CCCCC1>CN(C1C=CN=CC=1)C.ClCCl>[CH3:23][Si:24]([CH3:29])([CH3:28])[CH2:25][CH2:26][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Br:1])[C:3]([Cl:22])=[CH:4][C:5]=1[O:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16]

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 180132-(Trimethylsilyl)ethanolHCID 686032665-Bromo-2-(3-tert-butoxycarbonyl-propoxy)-4-chloro-benzoic acid

生成物 1

HCID 686027085-Bromo-2-(3-tert-butoxycarbonyl-propoxy)-4-chloro-benzoic acid 2-trimethylsilanyl-ethyl ester収率 109.8%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To a stirring dichloromethane solution (40 mL) containing 5-bromo-2-(3-tert-butoxycarbonyl-propoxy)-4-chloro-benzoic acid (2.3 g, 5.9 mmol) and 2-(trimethylsilyl)-ethanol (1.8 g, 8.9 mmol), dicyclohexyl-carbodiimide (1.83 g, 8.9 mmol) and DMAP (108 mg, 0.9 mmol) were added. The mixture was stirred at rt for 16 hrs and was concentrated. The residue was purified via silica gel flash chromatography (eluting with 20% ethyl acetate in hexane) to afford 5-bromo-2-(3-tert-butoxycarbonyl-propoxy)-4-chloro-benzoic acid 2-trimethylsilanyl-ethyl ester (3.2 g). MS ion (APCI): 482.0, 441.0, 410.9. tR=3.61 min (method 1)

後処理

  1. additionwere added
  2. concentrationwas concentrated
  3. customThe residue was purified via silica gel flash chromatography (eluting with 20% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-e83803ab001d4ee1bf9586d1e01fc2fe
出典データセット
uspto-grants-2015_02
特許番号
US08952161B2

反応ノート

読み込み中…