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21st March 2012 @ 00:18
Product obtained.

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Synthesis of TCMDC-123794 using the method used for PMY 10-6. Acid chloride batch PMY 32-3.

PMY11-5.png

Reaction start time: 15.30 21/03/12
PMY 9-1 was dried under reduced pressure for 4 hours prior to reaction (420 mg, 1.61 mmol, 2.0 equiv.) and was stirred with 4-DMAP (120 mg, 0.98 mmol, 0.5 equiv.) and DIPEA (0.30 mL, 1.72 mmol, 2.2 equiv.) in anhydrous THF (3 mL). PMY 32-3 (50 mg/mL in THF, 4 mL, 0.79 mmol, 1 equiv.) was added dropwise over 5 minutes to the orange solution at room temperature. A precipitate forms within 10 minutes. After 1 hour, product is forming, SM still remains. No change after 18 hours at room temperature. Reaction was adsorbed onto silica and purified by chromatography (50% EtOAc/hexane). After a long running column, 2 fractions containing product were collected, PMY 11-6-A and -B. Both triturated (Et2O and EtOAc) to obtain white powder PMY 11-6-A (69 mg) and PMY 11-6-B.

TLC (66% EtOAc/hexane) visualised with UV and vanillin:
TLC 1 hour
TLC 18 horus
TLC 2 hours

Left to right: 1 hr; JRC 2-1, M, RM, M, PMY 9-1. 2 hr; JRC 2-1, M, RM, M, PMY 11-5. 18 hr; JRC 2-1, M, RM.

Mass Spec:
ESI mass spec


See also:
Synthesis of TCMDC-123812 via acid chloride (PMY 10-6)
Synthesis of TCMDC-123794 via acid chloride, improved method (PMY 11-5)
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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TLC 1 hour
TLC 2 hours
TLC 18 horus
ESI mass spec