Methanol → D-Leucine, methyl ester

HRID 77320

Reaktionsgleichung

Reaktionsgleichung von HRID 77320
C(OC([NH:8][C@H:9]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:10]([OH:12])=[O:11])=O)(C)(C)C.S(Cl)(Cl)=O.[CH3:21]O>>[CH3:21][O:12][C:10](=[O:11])[C@H:9]([NH2:8])[CH2:13][CH:14]([CH3:16])[CH3:15]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 637604tert-Butoxycarbonyl-D-leucine

Produkt 1

HCID 89967D-Leucine, methyl ester

Versuchsvorschrift

To a solution of (R)-2-tert-butoxycarbonylamino-4-methyl-pentanoic acid (2 g, 8.7 mmol) in methanol (20 mL) is added thionyl chloride (2.59 g, 21.7 mmol). The reaction mixture is refluxed for 2 h. The reaction mixture is cooled to room temperature and concentrated in vacuo. The crude product is carried on without any further purification. 1H NMR (400 MHz, MeOD): δ 1.00 (q, 6H, J=3 Hz), 1.7-1.9 (m, 3H, J=7.7 Hz), 3.85 (s, 3H), 4.0 (t, 1H).

Aufarbeitung

  1. temperatureThe reaction mixture is refluxed for 2 h
  2. concentrationconcentrated in vacuo
  3. customThe crude product is carried on without any further purification

Quellen und Nachweise

ORD-Eintrag
ord-14e00b9ebc264711ae9b0cd93e1f31b4
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841291B2

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