Methyl iodide → HCID 76850178, Verbindung

HRID 1171962Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1171962
IC.[C:3]([O:7][C:8]([NH:10][C@@H:11]([CH2:15][C:16]#[N:17])[C:12]([OH:14])=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH2:18]1CCN2C(=NCCC2)CC1.OS([O-])(=O)=O.[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[CH3:18][O:13][C:12](=[O:14])[C@@H:11]([NH:10][C:8]([O:7][C:3]([CH3:6])([CH3:5])[CH3:4])=[O:9])[CH2:15][C:16]#[N:17]

Komponenten

8

Edukt 4

HCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516920Potassium bisulfateHCID 7019873Boc-beta-cyano-L-alanine

Produkt 1

HCID 76850178HCID 76850178, VerbindungAusbeute 86,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Iodomethane (2.18 ml, 35.01 mmol) was added to a mixture of (S)-2-(tert-butoxycarbonylamino)-3-cyanopropanoic acid (5.00 g, 23.34 mmol) and DBU (3.67 ml, 24.51 mmol) in toluene (20 mL) at rt. The reaction was stirred at 50 C for 2 days. Water (20 mL), saturated KHSO4 (20 mL) and ethyl acetate (50 mL) were added. The organic layer was separated, washed with brine and dried over sodium sulfate. After removal of solvent, the residue was purified by chromatography (hexane:Ethyl acetate=2:1) to give the (S)-methyl-2-(tert-butoxycarbonylamino)-3-cyanopropanoate as white solid (4.6 g, 86%). 1H NMR (400 MHz, d6-DMSO) δ7.64 (d, J=8.8 Hz, 1H), 4.39 (m, 1H), 3.66 (s, 3H), 2.96 (dd, J=16.8 Hz & 5.1 Hz, 1H), 2.85 (dd, J=16.8 Hz & 5.2 Hz, 1H), 1.40 (s, 9H).

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of solvent
  5. customthe residue was purified by chromatography (hexane:Ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-a49283446fa94e4398bd2209b4db3a85
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07829665B2

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