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Pantathenamide Mimics
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24th August 2018 @ 15:28
Pantathenamide Mimics: 5
Reagents Mass (Volume) Mmols
4-bromo-1-butyne 4.21g (2.97mL)  31.67
Sodium Azide 3.09g  47.5
DMF 70mL  


1. The materials was left to stir overnight at room temperature to produce the azide. 


Theoretical Yield (Azide) = 3.01grams


Reagents Mass (Volume) Mmols
4-nitrile-1-butyne 3.01g 31.67
Triphenylphosphine 13.705g 52.25
Water (1mL)  


2. The materials was left to stir overnight at room temperature to produce the amine. 


1. TLC analysis of mobile phase (see experiment 1) stained with nin hydrin confirmed the amine. UV analysis also confirmed the product (FM 5/1)

Mass of Product = 13.4g

Attached Files
22nd August 2018 @ 13:56
Pantathenamide Mimics: 4

Aims of the experiment

1. Due to the volatility of the Azide (See 'the synthesis of Azides from bromine containing compound' experiment). We decided to convert FM 3/1 (Azide((see previous entry)) to the amine without purification.


Reagents Mass (Volume) Mmols
4-nitrile-1-butyne (FM3/1) 362.9mg 3.82
Triphenylphosphine 1.670g 6.314
H2O  (100 microlitres)  



1. FM 3/1 was added to a mixture of triphenylphosphine and water and stirred at room temperature for 18 hours.


1. TLC analysis of mobile phase (see previous experiment) was stained with nin Hydrin and another with KMnO4 confirmed the product. 

2. UV analysis also confirmed the product (FM 4/1). 


1. 10mL of 0.1M HCl was added to the product and extracted with (3x20mL EtOAc. TLC analysis confirmed product was mostly in the organic layer.

2. See attached files for schematic diagram


NMR analysis confirmed a 77% yield of the amine

Peak @ 3.122; J= 6.667, t=2H

Peak @ 2.58 J= 2.7, 4.0, dt =2H

Peak @ 2.45, J= 2.3336, t= H



Palladium-Catalysed Cyclisation of N-Alkynyl Aminomalonates Supporting Information

Attached Files
22nd August 2018 @ 13:46
Pantathenamide Mimics: 3
Reagents Mass (Volume) Mmols
4-bromo-1-butyne 508mg (0.36mL) 3.82
Sodium Azide 372.9mg 5.74
DMF 10mL  


1. The materials was left to stir at room temperature for 18 hours (overnight) to produce the azide (FM 3/1).



1. No workup was carried out due to the volatility of the azide product. TLC and NMR results (see attached files) showed the reaction had gone to completion. 

Attached Files
22nd August 2018 @ 13:14
Pantathenamide Mimics: 2


Reagents Mass (Volume) Mmols
4-bromo-1-butyne 519mg (0.36mL) 3.9
Sodium Azide 381mg 5.86
N-methyl pyrollidone (11mL)  


1. These were left in a round bottom flask to stir at 90oC for 4 hours. The Azide (FM 2/1) was produced.


1. The Azide (FM2/1) was cooled to room temperature and H2O was added

2. FM 2/1 was extracted with EtOAc (4x 50mL).

3. This was washed with brine (1x 15mL) and purified via rotary evaporation to produce a brown viscous liquid. 


Mass of FM 2/1 = 4.11g

Theoretical Yield = 370.9mg

Percentage Yield = 1108%

Attached Files
22nd August 2018 @ 12:22
Pantathenamide Mimics: 1
Reagents Volume (Weight) Mmols
4-Bromo-1-butyne 0.35mL (500mg) 3.76
Sodium Azide 273mg 4.2




1) Sodium Azide in DMSO was added along with 4-bromo-1-butyne (FM SM) and a magnetic stirring bar. Mixture was stirred at room temperature until reaction had fully dissolved. 

2) Mixture observed under TLC (Mobile Phase: 70% DCM, 30% Petroleum ether). 4-bromo-1-butyne was observed under UV while 4-nitrile-1-butyne observed under KMnO4.

3) 15mL of H2O was added to product (FM 1/1) and extracted with Diethyl-ether (3x 30mL).

4) Extracted solvent was washed with H2(2x 15mL) + brine (1x 15mL)

5) Organic layer was dried with excess MgSO4 and filtered using a vacuum.


Mass of FM 1/1 = 75mg

Theoretical Yield = 357.2mg 

Percentage Yield = 20.9%



As a result of the low yield, the Aqueous phase was re-extracted with diethyl ether (5x 30mL) and solvent was filtered to produce an extra 99mg of product. (FM1/2).

Both FM1/1 and FM1/2 were discovered to be volatile at room temperature. See NMR spectrum below. 


NMR analysis confirmed our azide but a very low yield of the product. 


1) Synthesis: Practical procedure for the synthesis of Alkyl Azides. Alvarez et al. 

Attached Files