Reacción #4600

ord-8099b77f8ff84220a75161afb1f5b51b

Ecuación de reacción

COc1c(C)c2c(c(OC(N)=O)c1C/C=C(\C)CCC(=O)O)C(=O)OC2
E-6-(1,3-dihydro-4-carbamoyloxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoic acid
C(=NC1CCCCC1)=NC1CCCCC1
dicyclohexylcarbodiimide
OCCN1CCOCC1
N-(2-hydroxyethyl)morpholine
COc1c(C)c2c(c(OC(N)=O)c1C/C=C(\C)CCC(=O)OCCN1CCOCC1)C(=O)OC2
morpholinoethyl E-6-(1,3-dihydro-4-carbamoyloxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otroevaporated to dryness
  2. 2
    OtroThe residue is chromatographed on silica gel
  3. 3
    Lavadoeluting with 50:1 dichloromethane

Procedimiento

To 1.0 g of E-6-(1,3-dihydro-4-carbamoyloxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoic acid dissolved in 20 ml of dry THF is added 0.59 g of dicyclohexylcarbodiimide and 0.037 g of N-(2-hydroxyethyl)morpholine. The mixture is left at room temperature for 6 hours, then evaporated to dryness. The residue is chromatographed on silica gel, eluting with 50:1 dichloromethane:methanol, to give morpholinoethyl E-6-(1,3-dihydro-4-carbamoyloxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04727069uspto-grants-1988_02