Formaldehyde → Rifampicin

HRID 46717

反応式

HRID 46717 の反応式
[CH3:1][C:2]1[C:7]2[O:8][C@:9]3([CH3:49])[O:12][CH:13]=[CH:14][C@H:15]([O:47][CH3:48])[C@@H:16]([CH3:46])[C@@H:17]([O:42][C:43]([CH3:45])=[O:44])[C@H:18]([CH3:41])[C@H:19]([OH:40])[C@H:20]([CH3:39])[C@@H:21]([OH:38])[C@@H:22]([CH3:37])[CH:23]=[CH:24][CH:25]=[C:26]([CH3:36])[C:27]([NH:29][C:30]4[C:34](=[O:35])[C:4](=[C:5]([C:32](=[O:33])[CH:31]=4)[C:6]=2[C:10]3=[O:11])[C:3]=1[OH:50])=[O:28].C=O.[CH3:53]N1CN(C)CN(C)C1.CC1C2O[C@@]3(C)C(C=2C2C(O)=CC(NC(C(C)=CC=C[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)C=CO3)=O)=C(O)C=2C=1O)=O.[NH2:112][N:113]1[CH2:118][CH2:117][N:116]([CH3:119])[CH2:115][CH2:114]1>C(O)(=O)C.CN(C)C=O>[CH3:1][C:2]1[C:7]2[O:8][C@:9]3([CH3:49])[O:12][CH:13]=[CH:14][C@H:15]([O:47][CH3:48])[C@@H:16]([CH3:46])[C@@H:17]([O:42][C:43]([CH3:45])=[O:44])[C@H:18]([CH3:41])[C@H:19]([OH:40])[C@H:20]([CH3:39])[C@@H:21]([OH:38])[C@@H:22]([CH3:37])[CH:23]=[CH:24][CH:25]=[C:26]([CH3:36])[C:27]([NH:29][C:30]4[C:31](/[CH:53]=[N:112]/[N:113]5[CH2:118][CH2:117][N:116]([CH3:119])[CH2:115][CH2:114]5)=[C:32]([OH:33])[C:5]([C:6]=2[C:10]3=[O:11])=[C:4]([C:34]=4[OH:35])[C:3]=1[OH:50])=[O:28]

参加物

8

反応物 5

HCID 712FormaldehydeHCID 79521,3,5-Trimethyl-1,3,5-triazacyclohexaneHCID 813491-Amino-4-methylpiperazineHCID 6324616RifamycinHCID 6436726Rifamycin S

生成物 1

HCID 135398735Rifampicin

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6228Dimethylformamide溶媒

実験手順

7 g. Rifamycin S are dissolved in 25 ml. dimethylformamide, then, while stirring, there are successively added 2.4 g. acetic acid, 0.6 g. paraformaldehyde and 0.85 g. 1,3,5-trimethyl-hexahydro-1,3,5-triazine. The mixture is then kept at 50° C. for 3 hours until the reaction is completed, with the formation of 3-methyl-1,3-oxazino (5,6-c) rifamycin (thin layer chromatography on silica gel 60 F254 - Merck: blue spot at Rf 0.19, eluent chloroform:methanol 9:1 v/v). 3.1 g. 1-amino-4-methylpiperazine are then added and the reaction is continued at 50° C. for about 1 hour until it is completed, as demonstrated by the disappearance of the blue spot in the TLC. After treatment in the usual way, a high yield (7.2 g.) of rifampicin is obtained. It can easily be purified by crystallisation from acetone.

後処理

  1. waitthe reaction is continued at 50° C. for about 1 hour until it

出典と根拠

ORDレコード
ord-720ad38bec7f46d0aac4239ff9d6ccb0
出典データセット
uspto-grants-1979_11
特許番号
US04174320

関連ノート

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