Triethylamine → methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanoate

HRID 1363463Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1363463
C(N(CC)CC)C.[CH3:8][C:9]1([CH3:16])[C:13]([CH3:15])([CH3:14])[O:12][BH:11][O:10]1.O1CCOCC1.[C:23]([O:27][C:28]([NH:30][C@@H:31]([CH2:36][C:37]1[CH:42]=[CH:41][C:40](I)=[CH:39][CH:38]=1)[C:32]([O:34][CH3:35])=[O:33])=[O:29])([CH3:26])([CH3:25])[CH3:24]>C(OCC)(=O)C.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]>[C:23]([O:27][C:28]([NH:30][C@@H:31]([CH2:36][C:37]1[CH:38]=[CH:39][C:40]([B:11]2[O:12][C:13]([CH3:15])([CH3:14])[C:9]([CH3:16])([CH3:8])[O:10]2)=[CH:41][CH:42]=1)[C:32]([O:34][CH3:35])=[O:33])=[O:29])([CH3:26])([CH3:24])[CH3:25]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 312751,4-DioxaneHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 10319078N-Boc-4-iodophenylalanine methylester

Produkt 1

HCID 10949509methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

PdCl2(dppf) (127 mg), triethylamine (2.14 ml), 4,4,5,5-tetramethyl-1,3,2-dioxaborolan (1.13 ml) and 1,4-dioxane (21 ml) were added to methyl (2S)-2-[(t-butoxycarbonyl)amino]-3-(4-iodophenyl)propionate (1.8 g) and stirred at 100° C. for 14 hours. The reaction solution was diluted with ethyl acetate, washed with water and dried over magnesium sulfate to remove the solvent. The residue was purified with a silica gel chromatography (hexane-ethyl acetate) to obtain the title compound (1.05 g).

Aufarbeitung

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. customto remove the solvent
  4. customThe residue was purified with a silica gel chromatography (hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-630641e897694613a39edb3139fe4c3b
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07884204B2

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