Reaktion #461585

ord-41296acd823f4e30b817cb0f000853f6

Reaktionsgleichung

C=C(C)C(=O)Cl
Methacryloyl chloride
Cl.N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O
Glucosamine hydrochloride
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
O=N[O-].[Na+]
sodium nitrite
→
C=C(C)C(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO
product
C=C(C)C(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO
2-Deoxy-2 -methacrylamido-D-glucose

Edukte

C=C(C)C(=O)Cl
Methacryloyl chloride
Cl.N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O
Glucosamine hydrochloride
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
O=N[O-].[Na+]
sodium nitrite

Reagenzien

Keine

Lösungsmittel

O
H2O

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe reaction was carried out similar to the synthesis of 1

Vorschrift

Glucosamine hydrochloride ( 0.06 mol; 13.25 g), sodium carbonate (0.2 mol; 21.2 g) and sodium nitrite (0.2 g) were dissolved under nitrogen atmosphere at 0° C. in 100 ml of H2O. Methacryloyl chloride (0.12 mol; 13.0 g) was added under vigorous stirring. The reaction was carried out similar to the synthesis of 1 and gave the product as a white powder after two recrystallizations from water/ethanol/ether. Yield: 8.3-8.9 g (56-60%), p.m. (decomp.): 198°-199° C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05480790uspto-grants-1996_01