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5th November 2012 @ 00:26
Mnr: MNR51-60
EDC Coupling of MNR51 with Ammonium Hydroxide to give MNR54-1

See - Synthesis of AEW16-1
- Synthesis of MNR52-1
- Synthesis of MNR53-1

MNR54_scheme.png
MNR54-1_table.PNG

Hazard Assessment
HIRAC MNR54.pdf


Procedure

reaction on at 1120am 5/11/12

EDCI (0.080, 0.41 mmol) and HOBt (0.005 g, 0.03 mmol) were added to a solution of MNR51-1 (100 mg, 0.35 mmol) in DCM (5 mL) and the mixture was stirred for 20 minutes. Ammonium hydroxide(28%, 0.04 mL, 0.52 mmol) was added and the reaction mixture stirred at room temperature. After stirring overnight the TLC still showed signs of starting material but it was decided to work the reaction up. It was quenched with sodium bicarbonate (10 mL) and extracted with DCM (3 x 10 mL), dried over MgSO4, filtered and concentrated to give a brown oil (0.105 g)

TLC in 100% EtOAc
MNR54-1_rxn.JPG


Column 80-100% EtOAc/Hexance

Fracs 44-60 as a red oil - first NMR showed mainly product but with traces of EtOAc.

mnr54-1_frac44-60_1H.pdf
mnr54-1_frac44-60_13C.pdf


After another 5 hours on the hivac - 0.034 g, 0.118 mmol, 34%

NMR
mnr54-1_frac44-60_hivac_1H.pdf
mnr54-1_frac44-60_hivac_13C.pdf
mnr54-1_hivac.zip

mnr54-1_frac44-60_19F.pdf
mnr54-1_rerun.zip
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Attached Files
HIRAC MNR54.pdf
MNR54-1_table.PNG
MNR54_scheme.png
mnr54-1_frac44-60_1H.pdf
mnr54-1_frac44-60_13C.pdf
MNR54-1_rxn.JPG
mnr54-1_hivac.zip
mnr54-1_frac44-60_hivac_1H.pdf
mnr54-1_frac44-60_hivac_13C.pdf
mnr54-1_frac44-60_19F.pdf
mnr54-1_rerun.zip