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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

IR 

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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23rd April 2013 @ 01:07
Mnr: 11-20
As for
Synthesis of MNR11-17
and
Synthesis of MNR11-16

Starting material from
Preparation of the dimethoxy Ugi-intermediate (MNR8-5)

MNR11-18%20scheme.png

MNR11-18%20table.PNG

Hazard and Risk Assessment:
HIRAC MNR11.pdf


Procedure:
To a solution of MNR8-5 (4.88 g, 10.5 mmol) in toluene (35 mL) at room temperature was added methanesulfonic acid (1.47 mL, 22.58 mmol) and the mixture was refluxed for 1 hour. The reaction was allowed to cool to room temperature and was quenched with saturated sodium carbonate and extracted with EtOAc (50 mL x 3). The organic fractions were dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the crude as a thick orange oil.

Crude - 3.965 g, 101 %

TLC
100% EtOAc. Starting material, co=spot, reaction mixture after work up
2013-04-22 16.41.25.jpg


NMR
mnr11-18_crude_vs_mnr11-17.pdf
mnr11-18_crude_1H.pdf
mnr11-18_crude.zip


Conclusion
Crude product taken on to the next step without further purification.

Hydrolysis of MNR11-18 to give MNR26-7

Strings
Starting material
InChI=1S/C25H40N2O6/c1-5-32-24(33-6-2)18-27(25(29)20-10-8-7-9-11-20)17-23(28)26-15-14-19-12-13-21(30-3)22(16-19)31-4/h12-13,16,20,24H,5-11,14-15,17-18H2,1-4H3,(H,26,28)
Product
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
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