Reaktion #1668249

ord-19db2c99270b4fa7a45a6efa64932d49

Reaktionsgleichung

CC(=O)O[C@]1(C(C)=O)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)[C@@H]5C[C@@H]5[C@]4(C)[C@H]3[C@H](O)C[C@@]21C
6-chloro-11α-hydroxy-17-acetoxy-1α,2α-methylene-4,6-pregnadiene-3,20-dione
CC(=O)O[C@]1(C(C)=O)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)[C@@H]5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C
6-chloro-17-acetoxy-1α,2α-methylene-4,6-pregnadiene-3,20-dione
O=C1CCC(=O)O1
succinic acid anhydride
→
CC(=O)O[C@]1(C(C)=O)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)[C@@H]5C[C@@H]5[C@]4(C)[C@H]3[C@H](OC(=O)CCC(=O)O)C[C@@]21C
(6-chloro-17-acetoxy-3,20-dioxo-1α,2α-methylene-4,6-pregnadien-11α-yl) hydrogen succinate

Edukte

CC(=O)O[C@]1(C(C)=O)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)[C@@H]5C[C@@H]5[C@]4(C)[C@H]3[C@H](O)C[C@@]21C
6-chloro-11α-hydroxy-17-acetoxy-1α,2α-methylene-4,6-pregnadiene-3,20-dione
CC(=O)O[C@]1(C(C)=O)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)[C@@H]5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C
6-chloro-17-acetoxy-1α,2α-methylene-4,6-pregnadiene-3,20-dione
O=C1CCC(=O)O1
succinic acid anhydride
—
A9

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeAfter purification by way of the sodium salt, 230 mg

Vorschrift

0.433 g. of 6-chloro-11α-hydroxy-17-acetoxy-1α,2α-methylene-4,6-pregnadiene-3,20-dione -- prepared from 6-chloro-17-acetoxy-1α,2α-methylene-4,6-pregnadiene-3,20-dione by microbiological hydroxylation as described in the following paragraph -- is reacted analogously to A9 with succinic acid anhydride and worked up. After purification by way of the sodium salt, 230 mg. of (6-chloro-17-acetoxy-3,20-dioxo-1α,2α-methylene-4,6-pregnadien-11α-yl) hydrogen succinate is obtained as a foam. UV: ε280 = 15,500.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US03935245uspto-grants-1976_01