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14th February 2012 @ 06:07
Target synthesised in 34% yield. 05/03/12 Purified further by trituration (Et2O) to obtain the pure product as a white powder (28 mg).

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Synthesis of TCMDC-123794 using the method used for MY 31-5 and PMY 34-1 for the preparation of the acid chloride. Acid chloride batch JRC 3-1.

PMY11-5.png

Reaction start time: 17.30 14/02/12
PMY 9-1 (100 mg, approx 0.38 mmol, approx 1.2 equiv. Contains slight impurity) and DIPEA (0.16 mL, 1.22 mmol, 2.3 equiv.) were stirred in dry THF (2 mL). A solution of acid chloride JRC 3-1 (80 mg, 0.32 mmol, 1 equiv.) in THF (3 mL) was added to the mixture and the reaction heated to 80 °C. After 17 hours, TLC shows new products and SM. 4-DMAP (approx. 20 mg, 0.16 mmol, 0.5 equiv.) added. After a further one hour, reaction still shows SM by TLC. Cooled to room temperature and concentrated under reduced pressure. Residues (orange oily solid) purified by chromatography (45% EtOAc/hexane, then 2% MeOH/DCM) gave impure product (80 mg) as a yellow solid. Further chromatography (55-100% EtOAc/hexane) gave the product (52 mg, 34%) as a off-white crystals. Mostly pure by 1H NMR.

TLC (10% MeOH/DCM) visualised with UV and vanillin:
TLC 17 hours

left plate, 17 hours. Right plate, 18 hours.

NMR:
1H NMR after 1st column
1H NMR triturated impurities
1H NMR triturated
1H NMR after 2st column


Mass Spec:
ESI mass spec


See also:
Coupling of pyrrole carboxylic acid PMY 8-4 and glycinamide derivative PMY30-3 (PMY 34-1)
Coupling of pyrrole acid chloride PMY 32-2 and glycinamide (PMY 31-5)
Synthesis of TCMDC-123794 via acid chloride (PMY 11-2)
Synthesis of TCMDC-123794 via acid chloride (PMY 11-4)
Synthesis of TCMDC-123794 via acid chloride (PMY 11-4)

Risk and Hazard Assessment:
See: Synthesis of TCMDC-123812 via acid chloride (PMY 10-1)
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Attached Files
Scheme
TLC 17 hours
1H NMR after 1st column
1H NMR after 2st column
1H NMR triturated
1H NMR triturated impurities
ESI mass spec