Ethyl bromoacetate → Tert-butyl 2-(2-ethoxy-2-oxoethyl)hydrazine-1-carboxylate

HRID 1627199

Reaktionsgleichung

Reaktionsgleichung von HRID 1627199
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:8]([O:12][C:13](=[O:16])[NH:14][NH2:15])([CH3:11])([CH3:10])[CH3:9]>O>[CH2:6]([O:5][C:3](=[O:4])[CH2:2][NH:15][NH:14][C:13]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:16])[CH3:7]

Komponenten

4

Edukt 2

HCID 7748Ethyl bromoacetateHCID 70091tert-Butyl carbazate

Produkt 1

HCID 13434344Tert-butyl 2-(2-ethoxy-2-oxoethyl)hydrazine-1-carboxylateAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Ethyl bromoacetate 3 (6.97 mL, 62.8 mmol) was added to a stirred solution of tert-butylcarbazate 2 (24.9 g, 188.6 mmol) in water (25 mL) at room temperature. The mixture was stirred for 30 min. Water layer was then extracted with ethyl acetate (3×). Ethyl acetate extracts were pooled together and washed with brine. Ethyl acetate was evaporated under vacuum to get crude product which was purified by flash column chromatography using hexane:ethyl acetate (70:30) as an eluent (yield 70%). 1H NMR (500 MHz, CDCl3) 1.28 (3H, CH2—CH3, t), 1.45 (9H, C—CH3, s), 3.64 (2H, NH—CH2—CO, s), 4.20 (2H, CH2CH3, q); MS Anal. Mol. Wt. 218.25 (M+1).

Aufarbeitung

  1. extractionWater layer was then extracted with ethyl acetate (3×)
  2. washwashed with brine
  3. customEthyl acetate was evaporated under vacuum
  4. customto get crude product which
  5. customwas purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-632fadc7fdcc47aeb266649656096a00
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785499B2

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