Reaktion #86293

ord-a25ee7f6fb8a490a9993942bd0b23326

Reaktionsgleichung

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

Edukte

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

Reagenzien

Keine

Lösungsmittel

CO
Methanol

Reaktionsbedingungen

Temperatur
82.5°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigewith stifling at room temperature
  2. 2
    TemperaturThe reaction mixture is heated
  3. 3
    Temperaturcooled to room temperature
  4. 4
    SonstigeThe precipitated crystals are separated by filtration
  5. 5
    Waschenwashed with methanol and water
  6. 6
    Sonstigedried under reduced pressure

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09434758B2uspto-grants-2016_09