Reacción #549619

ord-bda66d698a5744e5a7d99312123aa390

Ecuación de reacción

CCOC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)[C@@H](OCC)C[C@]4(C)[C@H]3[C@H](NC(=O)OCC(Cl)(Cl)Cl)C[C@]12C
Ethyl 2β-ethoxy-3α-hydroxy-11α-(2,2,2-trichloroethoxy-carbonylamino)-5α-androstane-17β-carboxylate
CC(=O)OC(C)=O
acetic anhydride
→
CCOC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](OC(C)=O)[C@@H](OCC)C[C@]4(C)[C@H]3[C@H](NC(=O)OCC(Cl)(Cl)Cl)C[C@]12C
foam
CCOC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](OC(C)=O)[C@@H](OCC)C[C@]4(C)[C@H]3[C@H](NC(=O)OCC(Cl)(Cl)Cl)C[C@]12C
Ethyl 3α-acetoxy-2β-ethoxy-11α-(2,2,2-trichloroethoxycarbonylamino)-5α-androstane-17β-carboxylate

Reactantes

CCOC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)[C@@H](OCC)C[C@]4(C)[C@H]3[C@H](NC(=O)OCC(Cl)(Cl)Cl)C[C@]12C
Ethyl 2β-ethoxy-3α-hydroxy-11α-(2,2,2-trichloroethoxy-carbonylamino)-5α-androstane-17β-carboxylate
CC(=O)OC(C)=O
acetic anhydride

Reactivos

Ninguno

Disolventes

CCO
ethanol
c1ccncc1
pyridine

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otroevaporated

Procedimiento

Ethyl 2β-ethoxy-3α-hydroxy-11α-(2,2,2-trichloroethoxy-carbonylamino)-5α-androstane-17β-carboxylate (1.83 g) in pyridine (6 ml) was treated with acetic anhydride. After b 18 h. the reaction mixture was diluted with ethanol and evaporated to give a foam (1.91 g). A portion was purified by preparative t.l.c. in ethyl acetate/Petrol (1:2) to give the title compound, [α]D +30.7°, νmax 1724 cm-1.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04515786uspto-grants-1985_05