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

HRID 448927Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 448927
[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]

Komponenten

6

Edukt 3

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

Produkt 1

HCID 686027085-Bromo-2-(3-tert-butoxycarbonyl-propoxy)-4-chloro-benzoic acid 2-trimethylsilanyl-ethyl esterAusbeute 109,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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)

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-96ed783239bb47a1bd7d947386b31e8c
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481738B2

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