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

HRID 448927노트

반응식

HRID 448927 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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 (APCl): 482.0, 441.0, 410.9. tR=3.61 min (method 1)

후처리

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

출처 및 근거

ORD 기록
ord-96ed783239bb47a1bd7d947386b31e8c
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481738B2

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