반응 #86291

ord-56530e5dd603406890817f299bf356cb

반응 방정식

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

반응물

—
( 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

시약

없음

용매

CN(C)C=O
dimethylformamide
C1CCOC1
tetrahydrofuran

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    온도cooled in an ice bath
  2. 2
    기타SO2 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

실험 절차

(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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US09434758B2uspto-grants-2016_09