Réaction #86293

ord-a25ee7f6fb8a490a9993942bd0b23326

Équation de réaction

CS(=O)(=O)Cl
methanesulfonyl chloride
CC(=O)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C
hydrocortisone acetate
CN(C)C=O
N,N-dimethylformamide
c1ccncc1
pyridine
→
CC(=O)OCC(=O)[C@@]1(O)CCC2C3CCC4=CC(=O)CC[C@]4(C)C3=CC[C@@]21C
title compound
CC(=O)OCC(=O)[C@@]1(O)CCC2C3CCC4=CC(=O)CC[C@]4(C)C3=CC[C@@]21C
2-((10S,13S,17R)-17-hydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,10,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate

Réactifs

CS(=O)(=O)Cl
methanesulfonyl chloride
CC(=O)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C
hydrocortisone acetate
CN(C)C=O
N,N-dimethylformamide
c1ccncc1
pyridine

Réactifs

Aucun

Solvants

CO
Methanol

Conditions de réaction

Température
82.5°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Autrewith stifling at room temperature
  2. 2
    TempératureThe reaction mixture is heated
  3. 3
    Températurecooled to room temperature
  4. 4
    AutreThe precipitated crystals are separated by filtration
  5. 5
    Lavagewashed with methanol and water
  6. 6
    Autredried under reduced pressure

Mode opératoire

The title compound can be synthesized from hydrocortisone acetate according to the procedure disclosed in EP 0097328.405 g (1 mol) of hydrocortisone acetate is added to a mixture of 2 liters of N,N-dimethylformamide and 350 ml of pyridine, and with stifling at room temperature, 260 g of methanesulfonyl chloride is added. The reaction mixture is heated, maintained at 80 to 85° C. for 1 hour, and then cooled to room temperature. Methanol (7 liters) is added. The precipitated crystals are separated by filtration, washed with methanol and water, and dried under reduced pressure to give the title compound.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US09434758B2uspto-grants-2016_09