Reacción #74994

ord-1b42b8aa694d4037aa028ed71dae40f2

Ecuación de reacción

CN1CCN(N)CC1
1-amino-4-methylpiperazine
O=C(O)C(=O)O
Oxalic acid
CC(C)(C)N1CN(C(C)(C)C)CN(C(C)(C)C)C1
1,3,5-tri-(tert.-butyl)-hexahydro-1,3,5-triazine
CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(c3C2=O)C(=O)C=C(NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)C4=O
rifamycin S
→
CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(c(/C=N/N5CCN(C)CC5)c(O)c4c3C2=O)NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C
rifampicin

Reactantes

CN1CCN(N)CC1
1-amino-4-methylpiperazine
O=C(O)C(=O)O
Oxalic acid
CC(C)(C)N1CN(C(C)(C)C)CN(C(C)(C)C)C1
1,3,5-tri-(tert.-butyl)-hexahydro-1,3,5-triazine
CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(c3C2=O)C(=O)C=C(NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)C4=O
rifamycin S

Reactivos

Ninguno

Disolventes

CN(C)C=O
dimethylformamide

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    ExtracciónThe chloroform extract finally
  2. 2
    Otroobtained
  3. 3
    Concentraciónis concentrated to a small volume
  4. 4
    workup.ADDITIONdiluted with an appropriate mixture of ethyl acetate-acetone

Procedimiento

0.36 g. Oxalic acid and 1.0 g. 1,3,5-tri-(tert.-butyl)-hexahydro-1,3,5-triazine are added to a solution of 2.8 g. rifamycin S in 10 ml. dimethylformamide. The mixture is kept at 75° C. for about 1 hour, then 1.7 g. of acidified 1-amino-4-methylpiperazine are added directly, according to the process described in Example 7. The chloroform extract finally obtained is concentrated to a small volume and diluted with an appropriate mixture of ethyl acetate-acetone to give a high yield of pure rifampicin.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04174320uspto-grants-1979_11