Reaction #1583901

ord-ae39137507834ba3ac812ba0d61fb884

Reaction equation

CC(=O)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C
methyl prednisolone 21-acetate
→
CC(=O)OCC(=O)C1(O)CCC2C3C[C@H](C)C4=CC(=O)C=C[C@]4(C)C3=CC[C@@]21C
title product
CC(=O)OCC(=O)C1(O)CCC2C3C[C@H](C)C4=CC(=O)C=C[C@]4(C)C3=CC[C@@]21C
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

Reactants

—
( 14 )
CC(=O)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C
methyl prednisolone 21-acetate

Reagents

None

Solvents

CN(C)C=O
dimethylformamide
C1CCOC1
tetrahydrofuran

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturecooled in an ice bath
  2. 2
    OtherSO2 is bubbled into methanesulfonyl chloride
  3. 3
    workup.ADDITIONthe mixture is added dropwise to the solution
  4. 4
    workup.ADDITIONcontaining the solution of methyl prednisolone 21-acetate

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09198921B2uspto-grants-2015_12