Reaction equation
[O:1]=[C:2]([CH2:7][CH3:8])[CH2:3][C:4]([OH:6])=[O:5].II.ClCl.[CH3:13]O>[OH-].[Na+]>[O:1]=[C:2]([CH2:7][CH3:8])[CH2:3][C:4]([O:6][CH3:13])=[O:5]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Intermediates of formula 3 are prepared using methods known in the art. See for example U.S. Pat. No. 3,974,275 to Bossert et al., incorporated fully herein by reference. Additionally, certain intermediates of formula 3 are commercially available, e.g., methyl β-aminocrotonate. Under Claisen reaction conditions, acetone is reacted with methyl propionate in the presence of sodium ethoxide, followed by protonation with dilute HCl, to yield 2,4-hexadione (13). The resulting diketone is then oxidized to 3-oxopentanoic acid (14) by treatment with I2 or Cl2 in aqueous NaOH. The resulting acid is esterified with methanol to yield methyl 3-oxopentanoate (15). The ester is then heated with ammonia, removing water during the reaction to yield methyl 3-aminopent-2-eneoate (3).
Sources & evidence
- ORD record
- ord-5c51225de79c4870981c81da5c9b895a
- Source dataset
- uspto-grants-1988_08
- Patent number
- US04761420
Linked notes
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