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12th November 2012 @ 02:46
Mnr: mnr51-60

EDC Coupling of MNR55 with Ammonium Hydroxide to give MNR56-1

See - Synthesis of MNR55-1 - Synthesis of MNR54-1

Hazard Assessment

HIRAC MNR54.pdf

Procedure

reaction on at 1120am 5/11/12

EDCI (0.056, 0.29 mmol) and HOBt (0.003 g, 0.02 mmol) were added to a solution of MNR55-1 (0.07 g, 0.24 mmol) in DCM (3 mL) and the mixture was stirred for 20 minutes. Ammonium hydroxide(28%, 0.1 mL) was added and the reaction mixture stirred at room temperature. After stirring for 4 hours 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 white solid (0.084 g)

TLC in 100% EtOAc

SANY0019.JPG

Column - 100% EtOAc

Frac 5-17 as a white solid - needs further drying before final NMRs

product poorly soluble in CHCl3 and MeOH

Quick NMR's before going on holiday -

mnr56-1_frac5-17_1H_MeOD.pdf
mnr56-1_frac5-17_19F_MeOD.pdf
mnr56-1_frac5-17.zip

Overnight NMR in MeOD - still very poorly soluble

mnr56-1_frac5-17_13C.pdf
mnr56-1_overnight.zip

 

After further drying - 0.040 g, 0.14 mmol, 57%

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Attached Files
MNR56-1_table.PNG
MNR56_scheme.png
SANY0019.JPG
mnr56-1_frac5-17_1H_MeOD.pdf
mnr56-1_frac5-17_19F_MeOD.pdf
mnr56-1_frac5-17.zip
mnr56-1_overnight.zip
mnr56-1_frac5-17_13C.pdf