Acetyl chloride → (Acetyloxy)-carbamic acid tert-butyl ester

HRID 466187Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 466187
[OH:1][NH:2][C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].C(N(CC)CC)C.[C:17](Cl)(=[O:19])[CH3:18]>ClCCl>[C:17]([O:1][NH:2][C:3]([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:9])(=[O:19])[CH3:18]

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 97534tert-butyl N-hydroxycarbamate

Produkt 1

HCID 10058028(Acetyloxy)-carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The starting material is prepared as follows: tert-Butyl N-hydroxycarbamate (3.89 g, 29.2 mmol) is dissolved in 25 ml of dichloromethane and cooled to 0° C. To this is added triethylamine (3.25 g, 32.1 mmol) and acetyl chloride (2.29 g, 29.2 mmol) dropwise. The mixture is extracted with ether and the extracts are washed with aqueous 2N HCl, water, 10% sodium bicarbonate, water, dried (MgSO4) and evaporated. The resulting colorless oil is purified by silica gel chromatography (10% ethyl acetate/hexane) to give O-acetyl-N-tert-butoxycarbonylhydroxylamine as a colorless oil.

Aufarbeitung

  1. customThe starting material is prepared
  2. extractionThe mixture is extracted with ether
  3. washthe extracts are washed with aqueous 2N HCl, water, 10% sodium bicarbonate, water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe resulting colorless oil is purified by silica gel chromatography (10% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-0ec37788ff9f44f5826a6fdd931eb830
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05155130

Notizen zur Reaktion

Wird geladen…