反応 #1583901

ord-ae39137507834ba3ac812ba0d61fb884

反応方程式

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

反応物

—
( 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

試薬

なし

溶媒

CN(C)C=O
dimethylformamide
C1CCOC1
tetrahydrofuran

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    温度cooled in an ice bath
  2. 2
    その他SO2 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

実験手順

(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.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US09198921B2uspto-grants-2015_12