Reaktion #94828

ord-4e98e46d8be14dc0b62c0c3aef402f49

Reaktionsgleichung

COC(=C1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)C3=CC[C@]12C)C(Cl)S(=O)c1ccccc1
21-chloro-20-methoxy-21-(phenylsulfinyl)pregna-4,9(11),17(20)-trien-3-one
COC(=C1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)C3=CC[C@]12C)C(Cl)S(=O)c1ccccc1
21-Chloro-20-methoxy-21-(phenylsulfinyl)pregna-4,9(11),17(20)-trien-3-one
[Na+].[OH-]
sodium hydroxide
O
water
ClCCl
methylene chloride
→
COC(=CCl)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)C3=CC[C@@]21C
title compound
COC(=CCl)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)C3=CC[C@@]21C
21-Chloro-17α-hydroxy-20-methoxypregna-4,9(11),20-trien-3-one

Edukte

COC(=C1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)C3=CC[C@]12C)C(Cl)S(=O)c1ccccc1
21-chloro-20-methoxy-21-(phenylsulfinyl)pregna-4,9(11),17(20)-trien-3-one
COC(=C1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)C3=CC[C@]12C)C(Cl)S(=O)c1ccccc1
21-Chloro-20-methoxy-21-(phenylsulfinyl)pregna-4,9(11),17(20)-trien-3-one
[Na+].[OH-]
sodium hydroxide
O
water
ClCCl
methylene chloride

Reagenzien

Keine

Lösungsmittel

C1CCOC1
THF
CO
methanol
CC(C)=O
acetone

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeis brought to 20°-25°
  2. 2
    SonstigeThe layers are separated
  3. 3
    Extraktionthe aqueous layer is extracted with methylene chloride (2×5 ml)
  4. 4
    Waschenwashed with water (10 ml)
  5. 5
    Trocknendried over sodium sulfate
  6. 6
    Einengenconcentrated under reduced pressure

Vorschrift

To a solution of 21-chloro-20-methoxy-21-(phenylsulfinyl)pregna-4,9(11),17(20)-trien-3-one (VI, Example 3, 100 mg) in THF (2 ml), methanol (0.45 ml) and acetone (0.3 ml) at 0° under nitrogen is added a solution of sodium hydroxide (5 N, 0.04 ml). The mixture is brought to 20°-25° and is allowed to stir for 24 hr. The mixture is poured into a mixture of water (25 ml) and methylene chloride (10 ml). The layers are separated and the aqueous layer is extracted with methylene chloride (2×5 ml). The organic extracts are combined and washed with water (10 ml), dried over sodium sulfate and concentrated under reduced pressure to give the title compound.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04342702uspto-grants-1982_08