Methyl iodide → N-Methyl--O--(9-phenyl-9H-fluoren-9-yl)-L-serine methyl ester

HRID 1275784Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1275784
[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:6][O:7][C:8]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH2:5].[C:28](=O)([O-])[O-].[K+].[K+].IC>C(#N)C.ClCCl>[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:6][O:7][C:8]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=2[C:15]2[C:20]1=[CH:19][CH:18]=[CH:17][CH:16]=2)[NH:5][CH3:28]

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 15516030O-(9-phenyl-9H-fluoren-9-yl)-L-serine methyl ester

Produkt 1

HCID 53855539N-Methyl--O--(9-phenyl-9H-fluoren-9-yl)-L-serine methyl esterAusbeute 4,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 0.8 g (2.2 mmol) of O-(9-phenyl-9H-fluoren-9-yl)-L-serine methyl ester (Example 4a, Step 2) and 1.2 g (8.9 mmol) of potassium carbonate in acetonitrile (5 mL) was added 0.17 mL (2.7 mmol) iodomethane and the mixture stirred at room temperature for 16 h. The mixture was dissolved in dichloromethane, filtered and after evaporation of the solvent the residue was chromatographed on silica gel with 60% ethyl acetate in hexanes to give 0.038 g (yield 4.5%) N-Methyl--O--(9-phenyl-9H-fluoren-9-yl)-L-serine methyl ester as an oil. 1H NMR (CDCl3, 300 MHz) δ: 7.67 (d, 2H), 7.45-7.10 (m, 11H), 3.73 (s, 3 H), 3.35-3.15 (m, 3H), 2.37 (s, 3H), 2.06 (s, 1H); 13C NMR (CDCl3, 75 MHz) 6: 173.2, 146.6, 146.4, 143.1, 140.6, 129.2, 129.1, 128.3, 128.1, 128.0, 127.1, 125.4, 125.3, 125.1, 119.9, 88.3, 63.8, 62.9, 51.7.

Aufarbeitung

  1. filtrationfiltered
  2. customafter evaporation of the solvent the residue
  3. customwas chromatographed on silica gel with 60% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-468d79d57ed541469845715aaf4c5165
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06162824

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