Reacción #1901065

ord-2995e9cd92bd4beca533396e2336eca0

Ecuación de reacción

CCCCCCCCCCCCCCCC(=O)NC[C@@H](OCc1ccc(OC)cc1)[C@@H]1C[C@@H](OC(C)=O)[C@H](n2ccc(=O)[nH]c2=O)O1
product
CCCCCCCCCCCCCCCC(=O)NC[C@@H](OCc1ccc(OC)cc1)[C@@H]1C[C@@H](OC(C)=O)[C@H](n2ccc(=O)[nH]c2=O)O1
1-[2-O-acetyl-3,6-dideoxy-5-O-[(4-methoxyphenyl)methyl]-6-[(1-oxohexadecyl)amino]-.beta.-D-ribo-hexofuranosyl]-2,4-(1H,3H)-pyrimidinedione
ClCCl.O=C(O)C(F)(F)F
methylene chloride trifluoroacetic acid
→
CCCCCCCCCCCCCCCC(=O)NC[C@@H](O)[C@@H]1C[C@@H](OC(C)=O)[C@H](n2ccc(=O)[nH]c2=O)O1
sought product
Rendimiento 24.0%
CCCCCCCCCCCCCCCC(=O)NC[C@@H](O)[C@@H]1C[C@@H](OC(C)=O)[C@H](n2ccc(=O)[nH]c2=O)O1
1-[2-O-acetyl-3,6-dideoxy-6-[(1-oxohexadecyl)amino]-.beta.-D-ribo-hexofuranosyl]-2,4-(1H,3H)-pyrimidinedione
Rendimiento 24.0%

Reactantes

CCCCCCCCCCCCCCCC(=O)NC[C@@H](OCc1ccc(OC)cc1)[C@@H]1C[C@@H](OC(C)=O)[C@H](n2ccc(=O)[nH]c2=O)O1
product
CCCCCCCCCCCCCCCC(=O)NC[C@@H](OCc1ccc(OC)cc1)[C@@H]1C[C@@H](OC(C)=O)[C@H](n2ccc(=O)[nH]c2=O)O1
1-[2-O-acetyl-3,6-dideoxy-5-O-[(4-methoxyphenyl)methyl]-6-[(1-oxohexadecyl)amino]-.beta.-D-ribo-hexofuranosyl]-2,4-(1H,3H)-pyrimidinedione
ClCCl.O=C(O)C(F)(F)F
methylene chloride trifluoroacetic acid
—
mixture

Reactivos

Ninguno

Disolventes

ClCCl
methylene chloride
CCOCC
ether

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe solution obtained
  2. 2
    Otroby evaporating
  3. 3
    Otrodrying
  4. 4
    OtroA product is obtained which
  5. 5
    Otroin pentane followed by evaporation again
  6. 6
    OtroThe product obtained
  7. 7
    Otrois chromatographed

Procedimiento

240 mg of the product of Stage A dissolved in 2 ml of methylene chloride is added to 7.5 ml of a mixture of methylene chloride/trifluoroacetic acid (9/1) under a nitrogen atmosphere. The solution obtained is agitated for 1 hour followed by evaporating and drying. A product is obtained which is taken up in ether then in pentane followed by evaporation again. The product obtained is chromatographed and 47 mg of sought product is obtained.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US06875752B2uspto-grants-2005_04