Methyl iodide → HCID 15092375, Verbindung

HRID 1504842Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1504842
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C@@H:13]([C:22]([OH:24])=[O:23])[NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25](=O)([O-])[O-].[K+].[K+].CI>CS(C)=O>[CH2:1]([O:8][C:9]([NH:11][CH2:12][C@@H:13]([C:22]([O:24][CH3:25])=[O:23])[NH:14][C:15]([O:17][C:18]([CH3:20])([CH3:21])[CH3:19])=[O:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2755950Boc-dap(Z)-OH

Produkt 1

HCID 15092375HCID 15092375, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A mixture of 3-{[(benzyloxy)carbonyl]amino}-N-(tert-butoxycarbonyl)alanine (100 g, 0.29 mol), potassium carbonate (82 g, 0.59 mol) and methyl iodide (42 g, 0.29 mol) in DMSO (1200 mL) was stirred at room temperature. After 12 hours, the reaction mixture was extracted with ethyl acetate, and the organics were separated and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to give methyl 3-{[(benzyloxy)carbonyl]amino}-N-(tert-butoxycarbonyl)alaninate. MS ESI calc'd. for C17H25N2O6 [M+H]+ 353. found 353. 1H NMR (400 MHz, CDCl3) δ 7.36-7.33 (m, 5H), 5.09 (s, 2H), 4.34-4.30 (m, 1H), 3.74 (s, 2H), 3.59 (t, J=6.0 Hz, 2H), 2.62 (s, 3H), 1.44 (s, 9H).

Aufarbeitung

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. customthe organics were separated
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-a645d5363d924632882a740fa7a93c2f
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216173B2

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