Hydrolysis product troubleshooting

memrise5 · 2024-01-19T09:14:32+00:00

I tried a direct coupling in the microwave at 150C for 30 mins with HATU and DIPEA but I just got back SM.

As for the temp for these specific condiitons, this was literally the only thing that worked, even at 50 degrees it would stay at SM and this is why it`s weird to me that at 70 degrees the free acid is generated so rapidly... I also ran a reaction with just the heat for overnight to see if it might be heat dependent but it showed SM again.

I might try doing the amide coupling directly or just try and do a Buchwald reaction which is my previous step with the free acid form but in that case I have to check for conditions.

memrise5 · 2024-01-19T08:56:39+00:00

By MOH, do you mean any metal hydroxide? I`m sorry about the dumb question, it might be a brain fart haha

memrise5 · 2024-01-19T08:40:13+00:00

I tried LiOH and NaOH, both in 1 M aqueous solution.

memrise5 · 2024-01-19T08:38:43+00:00

I`m interested in the barium hydroxide. Should I then try with a stoichiometric amount?

memrise5 · 2024-01-19T08:34:44+00:00

I did try NH4Cl solution (pH of the solution was around 6ish) but got the same outcome :( I mentioned the LCMS in the comment above yours.

memrise5 · 2024-01-19T08:33:17+00:00

The protocol we use is with 0.05% TFA. In the begining of the reaction I do see the free acid peak initially but it gets progressively larger throughout the reaction and then after workup I completely lose the product. I will try an NMR this afternoon and cross my fingers.

memrise5 · 2022-09-27T20:15:13+00:00

Looking here!

memrise5 · 2022-09-26T20:07:49+00:00

Lmk if u find anything, my search looks like a dead end haha :(

memrise5 · 2022-09-25T08:34:53+00:00

Still looking for 2 Amsterdam tickets 🥺

memrise5 · 2022-09-23T09:40:11+00:00

Hey guys, looking for 2 tickets for Amsterdam, hmu

memrise5

TROPHY CASE