Sodium Chloride → N-Farnesyl farnesyl carboxamide

HRID 463527Notes

Reaction equation

HRID 463527 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

HCID 54142715N-Farnesyl farnesyl carboxamideYield 86.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×HCID 8471TriethylamineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f5af81d0a344424c9e5b04c3e70b00f5
Source dataset
uspto-grants-1985_05
Patent number
US04520029

Reaction notes

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