Triethylamine → (2RS,3S)-3-tert-butyloxycarbonylamino-2-hydroxy-5-methylhexanoic acid
Reaction equation
[NH2:1][C@@H:2]([CH2:8][CH:9]([CH3:11])[CH3:10])[CH:3]([OH:7])[C:4]([OH:6])=[O:5].C(N(CC)CC)C.[C:19]([O:23][C:24](ON=C(C1C=CC=CC=1)C#N)=[O:25])([CH3:22])([CH3:21])[CH3:20]>O.O1CCOCC1>[C:19]([O:23][C:24]([NH:1][C@@H:2]([CH2:8][CH:9]([CH3:11])[CH3:10])[CH:3]([OH:7])[C:4]([OH:6])=[O:5])=[O:25])([CH3:22])([CH3:21])[CH3:20]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 3.22 g of (2RS, 3S)-3-amino-2-hydroxy-5-methylhexanoic acid and 3.08 ml of triethylamine in 30 ml of water was added a solution of 5.41 g of 2-(tert-butyloxycarbonyloxyimino)-2-phenylacetonitrile in 30 ml of dioxane, and the mixture was stirred for 16 hours at room temperature. To the reaction mixture was added 100 ml of water, and the mixture was extracted with ethyl acetate to remove neutral materials. The aqueous layer was acidified by adding citric acid, and the aqueous solution was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure to obtain 5.10 g of (2RS, 3S)-3-tert-butyloxycarbonylamino-2-hydroxy-5-methylhexanoic acid as a pale yellow oil.
Workup
- extractionthe mixture was extracted with ethyl acetate
- customto remove neutral materials
- additionby adding citric acid
- extractionthe aqueous solution was extracted with ethyl acetate
- washThe ethyl acetate layer was washed with a saturated sodium chloride aqueous solution
- dry with materialdried over anhydrous magnesium sulfate
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-7e713fd362b542da8d2ff727ecd7e75b
- Source dataset
- uspto-grants-1989_06
- Patent number
- US04841067
Reaction notes
Loading…