L-leucine cyclopentyl ester tosylate → HCID 53718217, Verbindung

HRID 548216

Reaktionsgleichung

Reaktionsgleichung von HRID 548216
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:12]1([O:17][C:18](=[O:25])[C@@H:19]([NH2:24])[CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:16][CH2:15][CH2:14][CH2:13]1>C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH:12]1([O:17][C:18](=[O:25])[C@@H:19]([NH2:24])[CH2:20][CH:21]([CH3:22])[CH3:23])[CH2:13][CH2:14][CH2:15][CH2:16]1

Komponenten

4

Edukt 1

HCID 86633653L-leucine cyclopentyl ester tosylate

Produkt 1

HCID 53718217HCID 53718217, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

A solution of (S)-2-amino-4-methyl-pentanoic acid cyclopentyl ester toluene-4-sulfonic acid (2.57 g, 0.013 mol) in DCM (5 ml) was washed with saturated aqueous NaHCO3 solution (2×3 ml). The combined aqueous layers were back extracted with DCM (3×4 ml). The combined organic layers were dried (MgSO4), and the solvent removed in vacuo to give a colourless oil (1.10 g, 80% yield). 1H NMR (300 MHz, CDCl3), δ: 0.90 (6H, t, CH3×2, J=6.4 Hz), 1.23-1.94 (11H, m, 5×CH2, CH), 3.38 (1H, dd, CH, J=8.4, 5.9 Hz), 5.11-5.22 (1H, m, CH).

Aufarbeitung

  1. extractionThe combined aqueous layers were back extracted with DCM (3×4 ml)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2d81640fe2084971b53d5dac39537d24
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07939666B2

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