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 221192Notes

Reaction equation

HRID 221192 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-f67ed5c980c44ecb99857191bb3d7581
Source dataset
uspto-grants-2012_06
Patent number
US08207151B2

Reaction notes

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