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Halite (NaCl) → N-Farnesyl farnesyl carboxamide

HRID 463527
笔记
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反应方程式

HRID 463527 反应方程式
[CH2:1]([C:16]([OH:18])=O)[CH:2]=[C:3]([CH2:5][CH2:6][CH:7]=[C:8]([CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[CH3:9])[CH3:4].[CH2:19]([NH2:34])[CH:20]=[C:21]([CH2:23][CH2:24][CH:25]=[C:26]([CH2:28][CH2:29][CH:30]=[C:31]([CH3:33])[CH3:32])[CH3:27])[CH3:22].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[Na+].[Cl-]>CN(C)C=O.O.C(N(CC)CC)C>[CH2:19]([NH:34][C:16]([CH2:1][CH:2]=[C:3]([CH2:5][CH2:6][CH:7]=[C:8]([CH2:10][CH2:11][CH:12]=[C:13]([CH3:14])[CH3:15])[CH3:9])[CH3:4])=[O:18])[CH:20]=[C:21]([CH2:23][CH2:24][CH:25]=[C:26]([CH2:28][CH2:29][CH:30]=[C:31]([CH3:33])[CH3:32])[CH3:27])[CH3:22]
参与物实验过程后处理来源与证据反应笔记

参与物

8

反应物 4

HCID 5234Halite (NaCl)HCID 199401二苯基膦叠氮化物HCID 3080630FarnesylamineHCID 537917614,8,12-Trimethyltrideca-3,7,11-trienoic acid

产物 1

HCID 54142715N-Farnesyl farnesyl carboxamide收率 86.4%

试剂、催化剂与溶剂 3

HCID 962
聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]
溶剂
HCID 6228N,N-二甲基甲酰胺溶剂3 次
HCID 8471三乙胺溶剂

实验过程

To a mixture of farnesyl carboxylic acid (7.15 g) and farnesylamine (6.95 g) in 20 ml of dimethylformamide was added at 0° C. to a solution of diphenylphosphorylazide (7.62 g) in 7 ml of dimethylformamide. Next, to this mixture was added a solution of triethylamine (3.20 g) in dimethylformamide (3 ml). The reaction mixture was kept at room temperature overnight and poured into water (900 ml). After adding table salt, this mixture was extracted with ethyl acetate. The organic phase was worked up as usual manner and gave pale yellow oil. This material was purified by silica gel chromatography by using a mixture of methanol:benzene (2:1) as the eluent and gave 11.20 g of the titled compound.

后处理

  1. extractionthis mixture was extracted with ethyl acetate
  2. customgave pale yellow oil
  3. customThis material was purified by silica gel chromatography
  4. additiona mixture of methanol:benzene (2:1) as the eluent

来源与证据

ORD记录
ord-f5af81d0a344424c9e5b04c3e70b00f5
来源数据集
uspto-grants-1985_05
DOI
10.6084/m9.figshare.5104873.v1
专利号
US04520029

反应笔记

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本页导航参与物实验过程后处理来源与证据反应笔记