Hydrochloric Acid → Methyl 6,6,6-trifluoro-5-hydroxynorleucinate hydrochloride
Reaction equation
[ClH:1].[F:2][C:3]([F:14])([F:13])[CH:4]([OH:12])[CH2:5][CH2:6][C@@H:7]([C:9]([OH:11])=[O:10])[NH2:8].[CH3:15]O>>[ClH:1].[F:2][C:3]([F:13])([F:14])[CH:4]([OH:12])[CH2:5][CH2:6][C@@H:7]([C:9]([O:11][CH3:15])=[O:10])[NH2:8]Participants
4
Procedure
1.4 ml of saturated hydrochloric acid in methanol were added to 150 mg (0.7 mmol) of rac-6,6,6-trifluoro-5-hydroxynorleucine (stereoisomer mixture), and the mixture was stirred under reflux overnight. The reaction solution was concentrated, another 1.5 ml of saturated hydrochloric acid in methanol were added and the mixture was stirred under reflux overnight. The reaction solution was concentrated and the residue was dried under high vacuum. This gave 185 mg (99% of theory) of the target compound.
Workup
- temperatureunder reflux overnight
- concentrationThe reaction solution was concentrated
- additionanother 1.5 ml of saturated hydrochloric acid in methanol were added
- stirringthe mixture was stirred
- temperatureunder reflux overnight
- concentrationThe reaction solution was concentrated
- customthe residue was dried under high vacuum
Sources & evidence
- ORD record
- ord-fccb93fb15a0462990f4a2d05e95feab
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946215B2
Reaction notes
Loading…