From: an40496@anon.penet.fi (Holden Caulfield)
Date: Sat, 27 Nov 1993 23:07:53 UTC
Subject: An amidation of lysergic acid.

For anyone who's interested, here's another route for amidation of lysergic acid. I don't know if it's at all practical - what is phenyl N-phenyl-phosphorylamidochloride? I don't know what "amidochloride" means. Is it available, or cheap, and does it require special handling precautions? Will the reaction be air- or water-sensitive? It's not for my use, anyway. I am just posting it here for interest. From Chemical Abstracts 109:

109:170694r Preparation of substituted amides of lysergic acid and its derivatives. Stuchlik, Josef; Cvak, Ladislav; Kejzlarova, Jana; Schreiberova, Magdalena; Krajicek, Alois; Cerny, Antonin. Czech. CS 246,643 (Cl. C07D457/06), 16 Nov 1987, Appl. 85/1,497, 04 Mar 1985; 5 pp.

The title compounds I(R=HO, R3R2N; R1=H, C1-4 alkyl, 1-hydroxy-2- C2-4 -alkyl; R2=H,C1-2 alkyl; R3=C1-4 alkyl;R4=H,C1-4 alkyl) are prepared by reaction of acid I(R=OH) (II) in the presence of phenyl N-phenylphosphorylamidochloride (III) with amine HNR1R2 (IV). I are suitable for therapeutic applications. Lysergic acid (10 g) was suspended in 10 mL CH2Cl2, 10 mL Et3N are added, and the suspension mixed 10 minutes at room temperature. Then, 12 g III and 4 g (S)-(+)-2-amino-1-butanol were added. After 1 hour stirring, the reaction mixture was extracted with 5% NaOH solution and water. The organic phase was dried and concentrated by evaporation to give 12.5 g crude methylergometrin.

                           COR
                           |
                          / \
                         ||  |
                         ||  N-R3
                    / \\/ \ /   
                   ||  |   |    
                   ||  |   |         
                    \ //\ / 
                     |  || 
                  R4-N--||  


                       I    
  

By the way, what routes are there for amidation of lysergic acid? I've heard of:

and there's an unusual LSD synthesis starting from elymoclavine (like lysergic acid except the COOH becomes CH2OH and the double bond is moved to next to where it is in lysergic acid) which uses MnO2 for in situ oxidation.
The Sputnik LSD Pages.



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