Methylprednisolone Acetate → 2-((6s,10r,13s)-17-Hydroxy-6,10,13-trimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3h-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate

HRID 58013Notes

Reaction equation

HRID 58013 reaction equation
[CH3:1][C@@H:2]1[C:14]2=[CH:15][C:16]([CH:18]=[CH:19][C@:13]2([CH3:20])[C@@H:12]2[C@H:4]([C@H:5]3[C@:9]([CH3:22])([CH2:10][C@@H:11]2O)[C@@:8]([OH:30])([C:23]([CH2:25][O:26][C:27]([CH3:29])=[O:28])=[O:24])[CH2:7][CH2:6]3)[CH2:3]1)=[O:17]>CN(C)C=O.O1CCCC1>[C:27]([O:26][CH2:25][C:23]([C:8]1([OH:30])[C@:9]2([CH3:22])[CH:5]([CH:4]3[C:12](=[CH:11][CH2:10]2)[C@:13]2([CH3:20])[C:14](=[CH:15][C:16](=[O:17])[CH:18]=[CH:19]2)[C@@H:2]([CH3:1])[CH2:3]3)[CH2:6][CH2:7]1)=[O:24])(=[O:28])[CH3:29]

Participants

4

Reactant 1

HCID 5877Methylprednisolone Acetate

Product 1

HCID 672842222-((6s,10r,13s)-17-Hydroxy-6,10,13-trimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3h-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

(see Tetrahedron Letters, 2001, 42 (14): 2639-2642). Alternatively, methyl prednisolone 21-acetate is dissolved in a mixture of dimethylformamide and tetrahydrofuran and cooled in an ice bath. SO2 is bubbled into methanesulfonyl chloride and the mixture is added dropwise to the solution containing the solution of methyl prednisolone 21-acetate. The title product can then be isolated by standard aqueous workup.

Workup

  1. temperaturecooled in an ice bath
  2. customSO2 is bubbled into methanesulfonyl chloride
  3. additionthe mixture is added dropwise to the solution
  4. additioncontaining the solution of methyl prednisolone 21-acetate

Sources & evidence

ORD record
ord-56530e5dd603406890817f299bf356cb
Source dataset
uspto-grants-2016_09
Patent number
US09434758B2

Reaction notes

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