反応 #74994

ord-1b42b8aa694d4037aa028ed71dae40f2

反応方程式

1-amino-4-methylpiperazine

Oxalic acid

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

反応物

1-amino-4-methylpiperazine

Oxalic acid

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

試薬

なし

溶媒

dimethylformamide

反応条件

詳細条件

See reaction.notes.procedure_details.

後処理

1
抽出The chloroform extract finally
2
その他obtained
3
濃縮is concentrated to a small volume
4
workup.ADDITIONdiluted with an appropriate mixture of ethyl acetate-acetone

実験手順

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.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US04174320uspto-grants-1979_11