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13th August 2012 @ 04:30
Starting material recovered according to TLC. To be resubjected to conditions using DMF as catalyst.

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Conversion of PMY 59-2-B oxazole carboxylic acid (impure) to primary amide via reaction of the acid chloride with ammonia.

PMY60-2.png

Reaction Start Time: 11.55 13/08/12
PMY 59-2-B (28 mg, 0.09 mmol, 1 equiv.) was stirred in PhMe (0.6 mL). Thionyl chloride (0.05 mL, 0.7 mmol, 7.8 equiv.) was added and the reaction stirred at room temperature. After 4 hours, the reaction was concentrated under reduced pressure twice from PhMe (2 mL). THF (4 mL) was added and ammonia gas introduced via a balloon. A colourless precipitate forms. The reaction was allowed to stir overnight under a ammonia atmosphere. TLC shows starting material.

No decomposition observed as for PMY 60-1. Reaction probably requires harsher activation conditions. DMF catalyst to be added next time. LC/MS confirms presence of starting material, no significant decomposition.

TLC (15% MeOH/DCM) visualised with UV and vanillin:
TLC overnight


LC/MS
LCMS


See also:
Hydrolysis of PMY 58-2 methyl ester (PMY 59-2)

Risk and Hazard Assessment:
See: Conversion of PMY 59-1 oxazole carboxylic acid to primary amide (PMY 60-1) and Synthesis of TCMDC-123812 via acid chloride (PMY 10-2)
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Scheme
TLC overnight
LCMS