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16th September 2013 @ 14:21

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Reaction information

*#Reaction file
OverllReactionScheme.cdx
 
*Reaction file type CDX 
*Procedure See Child Reaction Steps 
*Yield (%) N?A 
*Type of Yield N/A 
Reference(s)
L.Sayerpp27.pdf
 
Further information -

For multistep reactions (or their steps):

Overall reaction? True
For overall reaction - links to child reaction steps Reaction 56
Reaction 58
Reaction 78 
For step in multistep reaction - link to previous reaction step N/A 
For step in multistep reaction - link to following reaction step N/A 
Attached Files
16th September 2013 @ 14:09

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Reaction information

*#Reaction file
OverallReaction.cdx
 
*Reaction file type CDX 
*Procedure See Child Reaction Steps 
*Yield (%) N/A 
*Type of Yield N/A 
Reference(s)
Thesis L Sayer9-10.pdf
 
Further information

For multistep reactions (or their steps):

Overall reaction? True 
For overall reaction - links to child reaction steps Reaction 43.1
Reaction 43.2
Reaction 44
Reaction 45
Reaction 73
Reaction 46 
For step in multistep reaction - link to previous reaction step N/A
For step in multistep reaction - link to following reaction step N/A 
Attached Files
16th September 2013 @ 14:04

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Reaction information

*#Reaction file
ReactionScheme.cdx
 
*Reaction file type CDX 
*Procedure

α-Sulpho-β-alanine (0.064 g, 0.38 mmol, 1.5 equiv.) was dissolved in water (0.5 mL) and sodium bicarbonate (0.094 g, 1.13 mmol, 4.5 equiv.) was added.  The solution was stirred for 5 minutes before the reaction mixture from the previous reaction was added slowly dropwise at 0°C.

The reaction was stirred for 1 hour before TLV showed that no starting material remained.  The reaction was acidified (~pH 4) with 10% HCl solution and the precipitate was dissolved using acetonitrile and water.  The crude material was concentrated.

An attempt to purify the product by column chromatography was made (silica gel, 10% methanol in DCM), however it was concluded that reverse phase HPLC would be needed in order to purify the compound.

*Yield (%) -
*Type of Yield
Reference(s)
L.Sayerpp37-38.pdf
 
Further information

For multistep reactions (or their steps):

Overall reaction? True
For overall reaction - links to child reaction steps N/A 
For step in multistep reaction - link to previous reaction step N/A 
For step in multistep reaction - link to following reaction step N/A 
Attached Files
16th September 2013 @ 14:01

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Reaction information

*#Reaction file
ReactionScheme.cdx
 
*Reaction file type CDX 
*Procedure

To a stirred solution of 2-((3-(1-((3aR,6aR)-5-hexyl-4-phenyl-1,2,3,3a,6,6a-hexahydropentalen-3a-yl)vinyl)benzyl)oxy)acetic acid (assumed 82 mg from previous reaction) in DMF (0.6 mL) was added TSTU (54 mg, 0.18 mmol, 1 equiv.) and DIEA (0.07 mL, 0.36 mmol, 2 equiv.).  The reaction was stirred overnight. TLC showed the presence of a small amount of starting material so extra TSTU was added (0.001 g) however, after 2 hours the starting material still remained in the reaction mixture.  This crude material was used in the next step of the synthesis immediately. 

*Yield (%) -
*Type of Yield
Reference(s)
L.Sayerpp37.pdf
 
Further information

For multistep reactions (or their steps):

Overall reaction? False 
For overall reaction - links to child reaction steps N/A 
For step in multistep reaction - link to previous reaction step Reaction 70 
For step in multistep reaction - link to following reaction step N/A
Attached Files
16th September 2013 @ 13:58

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Reaction information

*#Reaction file
ReactionScheme.cdx
 
*Reaction file type CDX 
*Procedure

To a stirred solution of tert-butyl 2-((3-(1-((3aR,6aR)-5-hexyl-4-phenyl-1,2,3,3a,6,6a-hexahydropentalen-3a-yl)vinyl)benzyl)oxy)acetate (95 mg, 0.18 mmol) in DCM (1.2 mL) was added TFA (0.3 mL) dropwise.  The reaction was stirred for 1 hour.

The reaction mixture was concentrated under reduced pressure and redissolved in chloroform before being concentrated again (a process that was repeated 3 times).  The crude product was used immediately in the next step of the synthesis.

*Yield (%) -
*Type of Yield -
Reference(s)
L.Sayerpp36-37.pdf
Further information

For multistep reactions (or their steps):

Overall reaction? False 
For overall reaction - links to child reaction steps N/A 
For step in multistep reaction - link to previous reaction step Reaction 69 
For step in multistep reaction - link to following reaction step Reaction 71
Attached Files