1,2-Dichloroethane → Methyl N-Hept-6-enoyl-3-methyl-L-valinate

HRID 389179

Reaktionsgleichung

Reaktionsgleichung von HRID 389179
[CH3:1][O:2][C:3](=[O:10])[C@H:4]([C:6]([CH3:9])([CH3:8])[CH3:7])[NH2:5].[C:11](O)(=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[CH2:17].C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1>CN(C=O)C.C([O-])(O)=O.[Na+]>[C:11]([NH:5][C@H:4]([C:3]([O:2][CH3:1])=[O:10])[C:6]([CH3:9])([CH3:8])[CH3:7])(=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[CH2:17]

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 707056-Heptenoic acidHCID 181649HOAtHCID 11309583Methyl L-tert-leucinate

Produkt 1

HCID 59571176Methyl N-Hept-6-enoyl-3-methyl-L-valinateAusbeute 80,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

A solution of L-t-leucine methyl ester (1.00 g, 6.89 mmol), 6-heptenoic acid (1.06 g, 8.26 mmol), EDC (1.58 g, 8.26 mmol) and HOAt (1.23 g, 8.26 mmol) in DMF (10 mL) was stirred at RT for 2 hours. The reaction mixture was diluted with aqueous saturated NaHCO3 (30 mL), and extracted with EtOAc (3×50 mL). The combined organic layers were washed with water (3×30 mL), brine (20 mL), dried over Na2SO4, filtered and concentrated. The residue was chromatographed on silica (5-50% EtOAc/hexane), to give the title compound (1.42 g). LRMS (ESI) m/z 256.3 [(M+H)+; calcd for C14H26NO3: 256.2].

Aufarbeitung

  1. extractionextracted with EtOAc (3×50 mL)
  2. washThe combined organic layers were washed with water (3×30 mL), brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica (5-50% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-0a373c9ecad14416ac060d77a282403f
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08377874B2

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