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 1496722Notes

Reaction equation

HRID 1496722 reaction equation
[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]

Participants

6

Reactant 4

HCID 1049PyridineHCID 5744Hydrocortisone AcetateHCID 6228DimethylformamideHCID 31297Methanesulfonyl chloride

Product 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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
82.5 °C

Procedure

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 stiffing 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.

Workup

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

Sources & evidence

ORD record
ord-0fa1c9cb694a45f296c4db15db677eab
Source dataset
uspto-grants-2015_12
Patent number
US09198921B2

Reaction notes

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