Sodium Hydroxide → HCID 7177179, compound
Reaction equation
[F:1][C:2]([F:13])([F:12])[CH2:3][CH2:4][CH:5]1[NH:9]C(=O)N[C:6]1=[O:11].[OH-:14].[Na+]>>[F:1][C:2]([F:13])([F:12])[CH2:3][CH2:4][C@@H:5]([C:6]([OH:14])=[O:11])[NH2:9]Participants
3
Procedure
5-(3,3,3-trifluoropropyl)imidazolidine-2,4-dione (0.9 g, 4.59 mmol) was dissolved in a 10 mL solution of aqueous NaOH (0.734 g in 10 mL H2O, 18.35 mmol). The solution was divided in 2 special vessels for microwave technology. The solution was heated by microwave in sealed vessels for 1 h. Microwave conditions: 15 min at about 100% power, 150° C., 50 psi, then 5 min at rest, 0% power. Repeat sequence twice or until reaction is done. Water and ammonia were removed from the reaction mixture in vacuo and the resulting crude 5,5,5-trifluoronorvaline (1.1 g, 140%) and NaOH mixture was used in the next reaction without further purification. Mass Spectrum (+ESI): 172 (M+H)+.
Workup
- temperatureThe solution was heated by microwave in sealed vessels for 1 h
- custom15 min
- customat about 100% power, 150° C., 50 psi
- custom5 min
- customRepeat sequence twice or until reaction
- customWater and ammonia were removed from the reaction mixture in vacuo
- customthe resulting crude 5,5,5-trifluoronorvaline (1.1 g, 140%) and NaOH mixture was used in the next reaction without further purification
Sources & evidence
- ORD record
- ord-a133ff57278d4e9b844b032aa03ff589
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07858658B2
Reaction notes
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