Triethylamine → Methyl 3-oxo-2-(pivalamido)butanoate

HRID 1897558Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1897558
Cl.[NH2:2][CH:3]([C:8](=[O:10])[CH3:9])[C:4]([O:6][CH3:7])=[O:5].[C:11](Cl)(=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C>C(Cl)Cl>[O:10]=[C:8]([CH3:9])[CH:3]([NH:2][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])[C:4]([O:6][CH3:7])=[O:5]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 23120881Methyl 2-amino-3-oxobutanoate hydrochloride

Produkt 1

HCID 57659743Methyl 3-oxo-2-(pivalamido)butanoateAusbeute 74,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of methyl 2-amino-3-oxobutanoate hydrochloride (0.50 g, 3.0 mmol) in CH2Cl2 (30 mL) was cooled in an ice bath. Pivaloyl chloride (0.37 mL, 3.0 mmol) and triethylamine (0.84 mL, 6.0 mmol) were slowly added, and the reaction was allowed to slowly warm to room temperature overnight. The reaction was washed with water, dried over Na2SO4, and concentrated under vacuum. The residue was purified by silica gel chromatography (0%-3% MeOH—CH2Cl2) to obtain methyl 3-oxo-2-(pivalamido)butanoate (0.48 g, 74% yield). 1H NMR (400 MHz, CDCl3) δ 6.82 (bs, 1H), 5.21 (d, J=6.1 Hz, 1H), 3.82 (s, 3H), 2.39 (s, 3H), 1.24 (s, 9H) ppm. LC/MS: m/z 216.5 (M+H)+ at 1.98 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Aufarbeitung

  1. washThe reaction was washed with water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by silica gel chromatography (0%-3% MeOH—CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-4a5d63d830d0428bbf1c5b2d73612444
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08519137B2

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