Methyl iodide → HCID 12149490, Verbindung

HRID 910723Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 910723
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:13][C:14]#[CH:15])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:16](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C=O)C>[CH3:16][O:11][C:10](=[O:12])[C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:13][C:14]#[CH:15]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 7009126(2R)-2-(((tert-butoxy)carbonyl)amino)pent-4-ynoic acid

Produkt 1

HCID 12149490HCID 12149490, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The commercially available compound, 2-(R)-tert-butoxycarbonylaminopent-4-ynoic acid (0.321 g, 1.50 mmol) was dissolved in anhydrous DMF (5 mL). To the solution was added cesium carbonate (0.54 g, 1.65 mmol) in one portion. The mixture was stirred at room temperature for 45 min before methyl iodide (0.20 mL, 3.00 mmol) was added, and further stirred for three hours. The reaction was quenched with water (10 mL). The organics was extracted with dichloromethane (2×30 mL), washed with water (3×50 mL), and dried over anhydrous sodium sulfate. The solvent was completely removed under vacuum. The residue was further dried under high vacuum over night and used in the next reaction without further purification. The product 23 was obtained as a colorless viscous oil (0.326 g, 95% yield). 1H NMR (300 MHz, CDCl3): δ 1.48 (s, 9H), 2.08 (t, J=2.6 Hz, 1H), 2.75 (t, J=6.3 Hz, 2H), 3.78 (s, 3H), 4.46 (m, 1H), 5.32 (br s, 5H).

Aufarbeitung

  1. additionwas added
  2. customThe reaction was quenched with water (10 mL)
  3. extractionThe organics was extracted with dichloromethane (2×30 mL)
  4. washwashed with water (3×50 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was completely removed under vacuum
  7. customThe residue was further dried under high vacuum over night
  8. customused in the next reaction without further purification

Quellen und Nachweise

ORD-Eintrag
ord-28aa824fdaa742ff8ee55caff9e937ec
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022210B2

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