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Pictet-Spengler route to Praziquantel
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23rd April 2013 @ 01:09
Mnr: 21-30

As for Hydrolysis of MNR11-16 to MNR26-4 Hydrolysis of MNR11-17 to MNR26-5 Starting material from Synthesis of MNR11-18

Hazard and Risk Assessment:

HIRAC MNR7.pdf

Procedure:MNR11-8 (3.96 g, 10.63 mmol) was dissolved in EtOH (21 mL) and HCl (1M) (110 mL) and heated to reflux for 2.5 hours. The solution was allowed to cool to room temperature then cooled in an ice bath, basified with NaOH pellets (approx 8 g, pellets used to minimise volume of aqueous material) to pH 12-13 and extracted with DCM (4 x 100 mL). The organic fractions were combined, dried over magnesium sulphate, filtered and concentrated under reduced pressure to give an orange crispy solid (1.008 g).

TLCReaction mixture after 2.5 hours ran in 100% EtOAc

2013-04-23 13.15.20.jpg

IRĀ 

5f rac IR MNR26-7.jpg

Strings Starting material InChI=1S/C21H28N2O4/c1-26-18-10-15-8-9-23-17(16(15)11-19(18)27-2)12-22(13-20(23)24)21(25)14-6-4-3-5-7-14/h10-11,14,17H,3-9,12-13H2,1-2H3 Product InChI=1S/C14H18N2O3/c1-18-12-5-9-3-4-16-11(7-15-8-14(16)17)10(9)6-13(12)19-2/h5-6,11,15H,3-4,7-8H2,1-2H3

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Attached Files
mnr26-7 table.PNG
MNR26-3 scheme.png
MNR26-7 scheme.png
2013-04-23 13.15.20.jpg
5f rac IR MNR26-7.jpg