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Sodium Chloride → N-Farnesyl farnesyl carboxamide

HRID 463527
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HRID 463527 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 5234Sodium ChlorideHCID 199401P,P-Diphenylphosphinic azideHCID 3080630FarnesylamineHCID 537917614,8,12-Trimethyltrideca-3,7,11-trienoic acid

생성물 1

HCID 54142715N-Farnesyl farnesyl carboxamide수율 86.4%

시약·촉매·용매 3

HCID 962
Water
용매
HCID 6228Dimethylformamide용매3회
HCID 8471Triethylamine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f5af81d0a344424c9e5b04c3e70b00f5
출처 데이터셋
uspto-grants-1985_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04520029

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