Réaction #2358551

ord-3b8f9ee181bd412aaeb0eee78b901aca

Équation de réaction

Cl
HCl
O=C(Cl)OCc1ccccc1
Cbz-Cl
CCOCOc1cc(OCc2ccccc2)c(-c2n[nH]c(=O)n2-c2ccc3c(ccn3C)c2)cc1C(C)C
3-(2-(benzyloxy)-4-(ethoxymethoxy)-5-isopropylphenyl)-4-(1-methyl-1H-indol-5-yl)-1H-1,2,4-triazol-5(4H)-one
CCN(C(C)C)C(C)C
DIPEA
CCOCOc1cc(OCc2ccccc2)c(-c2nn(C(=O)OCc3ccccc3)c(=O)n2-c2ccc3c(ccn3C)c2)cc1C(C)C
benzyl 3-(2-(benzyloxy)-4-(ethoxymethoxy)-5-isopropylphenyl)-4-(1-methyl-1H-indol-5-yl)-5-oxo-4,5-dihydro-1H-1,2,4-triazole-1-carboxylate

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    LavageWashed with water
  2. 2
    Extractionextracted with dichloromethane and solvent
  3. 3
    Autrewas removed
  4. 4
    AutreThe crude reaction mixture
  5. 5
    Autrewas carried over to the next reaction without further purification
  6. 6
    Températureheated it up to 65° C

Mode opératoire

Cbz-Cl was added to the solution of 3-(2-(benzyloxy)-4-(ethoxymethoxy)-5-isopropylphenyl)-4-(1-methyl-1H-indol-5-yl)-1H-1,2,4-triazol-5(4H)-one and DIPEA in dichloromethane and reaction solution was stirred for 2 h at room temperature. Washed with water and extracted with dichloromethane and solvent was removed. The crude reaction mixture was carried over to the next reaction without further purification. The reaction mixture was diluted by methanol and treated with concentrated HCl and heated it up to 65° C. Column chromatogram produced the desired benzyl 3-(2-(benzyloxy)-4-(ethoxymethoxy)-5-isopropylphenyl)-4-(1-methyl-1H-indol-5-yl)-5-oxo-4,5-dihydro-1H-1,2,4-triazole-1-carboxylate.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US09120745B2uspto-grants-2015_09