Nalpha-(9-fluorenylmethoxycarbonyl)-O-(9-phenyl-9H-fluoren-9-yl)-L-serine methyl ester → O-(9-phenyl-9H-fluoren-9-yl)-L-serine methyl ester

HRID 1275750Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1275750
[CH3:1][O:2][C:3](=[O:44])[C@H:4]([CH2:23][O:24][C:25]1([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:37]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[C:31]2[C:26]1=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:5]C(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O>N1CCCCC1>[CH3:1][O:2][C:3](=[O:44])[C@H:4]([CH2:23][O:24][C:25]1([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:31]=2[C:32]2[C:37]1=[CH:36][CH:35]=[CH:34][CH:33]=2)[NH2:5]

Komponenten

3

Edukt 1

HCID 15516029Nalpha-(9-fluorenylmethoxycarbonyl)-O-(9-phenyl-9H-fluoren-9-yl)-L-serine methyl ester

Produkt 1

HCID 15516030O-(9-phenyl-9H-fluoren-9-yl)-L-serine methyl esterAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8082PiperidineLösungsmittel

Versuchsvorschrift

The crude Nα -(9-fluorenylmethoxycarbonyl)-O-(9-phenyl-9H-fluoren-9-yl)-L-serine methyl ester from Step 1 (Method A) was dissolved in piperidine (5 mL) and the mixture stirred at 60 (C for 0.5 h. After evaporation of the solvent the residue was chromatographed on silica gel with ethyl acetate to give 6.96 g (yield 97%) O-(9-phenyl-9H-fluoren-9-yl)-L-serine methyl ester as a viscous oil. 1H NMR (CDCl3, 300 MHz) δ: 7.65 (d, 2H), 7.40-7.05 (m, 11H), 3.65 (s, 3H), 3.46 (t, 1H), 3.30-3.10 (m, 2H), 1.80 (br s, 2H); 13C NMR (CDCl3, 75 MHz) δ: 174.1, 146.4, 146.2, 142.7, 140.4, 129.0, 128.9, 128.1, 127.9, 126.9, 125.2, 125.1, 124.9, 119.8, 119.7, 88.1, 65.1, 54.6, 51.8, 51.7, 13.9.

Aufarbeitung

  1. customAfter evaporation of the solvent the residue
  2. customwas chromatographed on silica gel with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-d2ef2de472dd471ea60831d050cc0ec6
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06162824

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