HRID1415408

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID8016

N-Methyl-N-hydroxyethylamine

C3H9NO

$结构：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$

HCID6436726

Rifamycin S

C37H45NO12

PRODUCTS

生成物

$结构：CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(cc(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$

HCID6324616

Rifamycin SV

C37H47NO12

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID31275

1,4-Dioxane

C4H8O2

PROCEDURE

实验过程

10 g (0.13 mol) of N-methylethanolamine are added to a solution of 21 g (0.03 mol) of rifamycin-S in 20 ml of dioxan and the whole heated for 15 minutes on a boiling water bath. The batch is then evaporated to dryness in vacuo and the residue chromatographed on 2kg of silica gel, using chloroform as eluant. In addition to a dark-colored head zone, two strong, yellow-colored bands are observed. The eluate of the more slowly eluted band is evaporated and the residue crystallized from aqueous methanol. After three crystallizations from aqueous methanol there is obtained 3-N-methylethanol-amino)-rifamycin-SV in the form of coarse prisms melting at 218° C (with decomposition.

WORKUP

后处理

temperaturethe whole heated for 15 minutes on a boiling water bath
customThe batch is then evaporated to dryness in vacuo
customthe residue chromatographed on 2kg of silica gel
additionIn addition to a dark-colored head zone, two strong
customThe eluate of the more slowly eluted band is evaporated
customthe residue crystallized from aqueous methanol
customAfter three crystallizations from aqueous methanol

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-c4a699024f8f439d8291345532d8ac06
来源数据集: uspto-grants-1977_01
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04005077
来源说明: uspto-grants-1977_01

反应 SMILES

CNCCO.[CH3:6][C:7]1[C:12]2[O:13][C@:14]3([CH3:54])[O:17][CH:18]=[CH:19][C@H:20]([O:52][CH3:53])[C@@H:21]([CH3:51])[C@@H:22]([O:47][C:48]([CH3:50])=[O:49])[C@H:23]([CH3:46])[C@H:24]([OH:45])[C@H:25]([CH3:44])[C@@H:26]([OH:43])[C@@H:27]([CH3:42])[CH:28]=[CH:29][CH:30]=[C:31]([CH3:41])[C:32]([NH:34][C:35]4[C:39](=[O:40])[C:9](=[C:10]([C:37](=[O:38])[CH:36]=4)[C:11]=2[C:15]3=[O:16])[C:8]=1[OH:55])=[O:33]>O1CCOCC1>[CH3:6][C:7]1[C:12]2[O:13][C@@:14]3([CH3:54])[C:15]([C:11]=2[C:10]2[C:37]([OH:38])=[CH:36][C:35]([NH:34][C:32]([C:31]([CH3:41])=[CH:30][CH:29]=[CH:28][C@H:27]([CH3:42])[C@H:26]([OH:43])[C@@H:25]([CH3:44])[C@@H:24]([OH:45])[C@@H:23]([CH3:46])[C@H:22]([O:47][C:48]([CH3:50])=[O:49])[C@H:21]([CH3:51])[C@@H:20]([O:52][CH3:53])[CH:19]=[CH:18][O:17]3)=[O:33])=[C:39]([OH:40])[C:9]=2[C:8]=1[OH:55])=[O:16]