Iodine → 2-(N'-benzyloxycarbonyl-hydrazino)-2-methyl-propionic acid ethyl ester

HRID 39654

Reaktionsgleichung

Reaktionsgleichung von HRID 39654
[C:1]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:4])[NH:2][NH2:3].Br[C:14]([CH3:21])([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16].N1C=CC=CC=1.II>CN(C=O)C.C(OCC)(=O)C>[CH2:18]([O:17][C:15](=[O:16])[C:14]([NH:3][NH:2][C:1]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4])([CH3:21])[CH3:20])[CH3:19]

Komponenten

7

Edukt 4

HCID 807IodineHCID 1049PyridineHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 79242Benzyl carbazate

Produkt 1

HCID 152825792-(N'-benzyloxycarbonyl-hydrazino)-2-methyl-propionic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
97.5 °C

Versuchsvorschrift

Benzyl carbazate (25 g, 0.15 mol) was dissolved in 50 mL of DMF in a round bottom flask. The solution was heated to 95-100° C. From two separate addition funnels, ethyl 2-bromoisobutyrate (58.5 g, 0.3 mol) and pyridine (29.7 g, 0.375 mol, 30 mL) were added drop-wise separately and simultaneously over 30-120 minutes. Heating was continued if necessary to propel the reaction to completion. The reaction was monitored by TLC (30% ethyl acetate in hexanes, I2 visualization). The mixture was allowed to cool, and then poured onto ice water. The aqueous mixture was extracted with ethyl ether, and the solvent was removed in vacuo. 2-(N′-benzyloxycarbonyl-hydrazino)-2-methyl-propionic acid ethyl ester was isolated, optionally after silica gel chromatography. 1H NMR (300 MHz, CDCl3) δ (ppm): 7.36 (br s, 5H), 6.6 (br s, 1H), 5.15 (br s, 2H), 4.2 (q, 2H), 1.3 (s, 6H), 1.25 (t, 3H). 1H NMR analysis alone is insufficient to ascertain the extent of the reaction.

Aufarbeitung

  1. customFrom two separate
  2. additionaddition funnels
  3. temperatureHeating
  4. customthe reaction to completion
  5. temperatureto cool
  6. additionpoured onto ice water
  7. extractionThe aqueous mixture was extracted with ethyl ether
  8. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-dd0158b28910400fb2c1313ddaee24f1
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524948B2

Verknüpfte Notizen

Wird geladen…