Hydrochloric Acid → Vigabatrin
Reaction equation
[CH:1]([CH:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1)=[CH2:2].Cl.FC(F)(F)C(O)=[O:13]>>[NH2:7][CH:3]([CH:1]=[CH2:2])[CH2:4][CH2:5][C:6]([OH:8])=[O:13]Participants
Procedure
In this reaction 5-vinyl-2-pyrrolidinone (structure 1) is subjected to an acidic hydrolysis thereby producing the desired compound, 4-amino-5-hexenoic acid (structure 2). This acidic hydrolysis is carried out using techniques known in the art. Typically, the 5-vinyl-2-pyrrolidinone is contacted with a strong acid such as hydrochloric acid or trifluoroacteic acid at a temperature above 60° C. in an aqueous solvent system. The 4-amino-5-hexenoic acid is recovered by concentration as is known in the art. The acidic hydrolysis followed by recrystallization produces a yield of 4-amino-5-hexenoic acid of 57-67%. The spent recrystallization liquor can be saved, concentrated, redissolved in ethanol and a second recrystallization can be carried out on this residue which increases the yield of final product by another 10-11%. The yield of 4-amino-5-hexenoic acid which is produced by this process is from 57-67% with one recrystallization and from 70-79% when a second recrystallization is carried out.
Workup
- customThis acidic hydrolysis
- customThe 4-amino-5-hexenoic acid is recovered by concentration
- customThe acidic hydrolysis
- customfollowed by recrystallization
Sources & evidence
- ORD record
- ord-75177970dcbf4578a0413e3beb62c62c
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06090979
Reaction notes
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