Triethylamine → 3-(2-tert-Butoxycarbonylamino-2-methylpropyl)benzoic acid methyl ester

HRID 1866508Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1866508
[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]([CH3:18])([CH3:17])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12](Br)[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C]=O>CO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][O:5][C:6](=[O:19])[C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([CH2:9][C:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:19])([CH3:18])[CH3:17])[CH:11]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 58907464tert-butyl N-[1-(3-bromophenyl)-2-methylpropan-2-yl]carbamateHCID 178418416HCID 178418416, Verbindung

Produkt 1

HCID 597135613-(2-tert-Butoxycarbonylamino-2-methylpropyl)benzoic acid methyl esterAusbeute 116,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of [2-(3-bromophenyl)-1,1-dimethylethyl]carbamic acid tert-butyl ester (Preparation 32) (7.0 g, 21 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1.74 g, 2.1 mmol) and triethylamine (5.94 ml, 43 mmol) in methanol (250 ml) was heated to 100° C. under 100 psi carbon monoxide for 12 hours. The reaction mixture was filtered through arbocel and the filtrate concentrated in vacuo and purified by flash column chromatography on silica gel eluting with dichloromethane:pentane (50:50 by volume) to afford the title compound as a yellow solid (3.76 g). 1H NMR (400 MHz, CDCl3) δ=7.92-7.90 (1H, m), 7.82 (1H, s), 7.35-7.34 (2H, m), 4.24 (1H, bs), 3.90 (3H, s), 3.05 (2H, s), 1.48 (9H, s), 1.26 (6H, s). LRMS (electrospray) m/z 208 [M+H−BOC]+

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through arbocel
  2. concentrationthe filtrate concentrated in vacuo
  3. custompurified by flash column chromatography on silica gel eluting with dichloromethane:pentane (50:50 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-df2fb9691c814956ac4f62187dde65ab
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07629358B2

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