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21st February 2012 @ 02:16
PS = Pictet-Spengler

***Experiment still in progress with regular updates. Last updated 21/02/12.

START: 21/02/12
FINISH:

Background

Scheme%20KAB8-14.png
Table%20KAB8-14.jpg

Hazard and Risk Assessment
As for KAB8-11 and KAB1-3.
Hazard and Risk Assessment KAB8-11
Hazard and Risk Assessment KAB1-3


Previous Related Experiments


Following Experiments


Procedure

21/02/12
General procedure. The peptide acetal Ugi-intermediate was dissolved in toluene before the addition of triflic acid at rt. The reaction vessel was immediately fitted with a condensing tube and placed in a pre-heated oil bath at 90 °C. The reaction mixture was reflux heated and the progress monitored by TLC against the relevant starting material and the expected product.

KAB8-14. Peptide acetal MNR10-2 (302.4 mg, 0.659 mmol), toluene (30 mL), TfOH (2.92 μL, 0.033 mmol, 5 mol%).

KAB1-5. Peptide acetal MNR8-3 (381.6 mg, 0.821 mmol), toluene (38 mL), TfOH (3.64 μL, 0.041 mmol, 5 mol%).

crude KAB8-14 (249.8 mg, 103%)

Monitoring the Reaction Progress by TLC
All TLCs were eluted with EtOAc/hexane, 5:3, v/v and stained with KMnO4. Time noted is the amount elapsed since the addition of acid.

Summary and Conclusion


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NOTES 21/02/12
KAB8-14 Flask: 49.1531 g

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Linked Posts
Attached Files
Scheme KAB8-14 & KAB1-5
Table KAB8-14 & KAB1-5