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Pyridine → 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

HRID 1186049
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Reaktionsgleichung

Reaktionsgleichung von HRID 1186049
[CH3:1][C:2]([O:4][CH2:5][C:6]([C@:8]1([OH:29])[C@@:12]2([CH3:28])[CH2:13][C@H:14](O)[C@@H:15]3[C@:25]4([CH3:26])[C:19](=[CH:20][C:21]([CH2:23][CH2:24]4)=[O:22])[CH2:18][CH2:17][C@H:16]3[C@@H:11]2[CH2:10][CH2:9]1)=[O:7])=[O:3].CN(C)C=O.N1C=CC=CC=1.CS(Cl)(=O)=O>CO>[C:2]([O:4][CH2:5][C:6]([C@:8]1([OH:29])[C@:12]2([CH3:28])[CH:11]([CH:16]3[C:15](=[CH:14][CH2:13]2)[C@:25]2([CH3:26])[C:19](=[CH:20][C:21](=[O:22])[CH2:23][CH2:24]2)[CH2:18][CH2:17]3)[CH2:10][CH2:9]1)=[O:7])(=[O:3])[CH3:1]
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Komponenten

6

Edukt 4

HCID 1049PyridineHCID 5744Hydrocortisone AcetateHCID 6228DimethylformamideHCID 31297Methanesulfonyl chloride

Produkt 1

HCID 130376572-((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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. customwith stifling at room temperature
  2. temperatureThe reaction mixture is heated
  3. temperaturemaintained at 80 to 85° c
  4. customThe precipitated crystals are separated by filtration
  5. washwashed with methanol and water
  6. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d275134b3c8d46c988e7846da4919a76
Quelldatensatz
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08673887B2

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