Triethylamine → Isopropyl (2Z)-3-amino-2-cyano-4-ethyl-2-hexenoate
Reaction equation
O/[C:2](/[CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[C:3](/[C:10]#[N:11])\[C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5].O=P(Cl)(Cl)Cl.C([N:24](CC)CC)C>C(Cl)Cl>[NH2:24]/[C:2](/[CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[C:3](/[C:10]#[N:11])\[C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5]Participants
Conditions
- Temperature
- 0 °C
Procedure
24.4 g (0.11 mol) of isopropyl (2Z)-3-hydroxy-2-cyano-4-ethyl-2-hexenoate were dissolved in CH2Cl2 and, at 25° C., 33.2 g (0.22 mol) of POCl3 were added. After cooling to 0° C., 43.8 g (0.44 mol) of triethylamine were added dropwise, and the mixture was stirred at 25° C. for 2 h. The solution was then concentrated and the residue was taken up in acetonitrile and cooled to 0° C., and 30 g (0.44 mol) of a 25 percent strength solution of ammonia were added dropwise. After 2 h of stirring, the mixture was concentrated to dryness, the residue was taken up in MTBE (methyl tert-butyl ether) and the organic phase was washed with NaOH and water, dried and concentrated. Purification by customary methods gave 10 g (40% of theory) of the title compound as a colorless solid (m.p. 140° C.).
Workup
- concentrationThe solution was then concentrated
- temperaturecooled to 0° C.
- addition30 g (0.44 mol) of a 25 percent strength solution of ammonia were added dropwise
- stirringAfter 2 h of stirring
- concentrationthe mixture was concentrated to dryness
- washthe organic phase was washed with NaOH and water
- customdried
- concentrationconcentrated
- customPurification by customary methods
Sources & evidence
- ORD record
- ord-1f3269e3fde34ad3a3eb295f921fe3db
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07851411B2
Reaction notes
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