Diisopropylethylamine → (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(3-cyanophenyl)propanoic acid
Reaction equation
Cl.[C:2]([C:4]1[CH:5]=[C:6]([CH:13]=[CH:14][CH:15]=1)[CH2:7][C@@H:8]([C:10]([OH:12])=[O:11])[NH2:9])#[N:3].C(N(C(C)C)C(C)C)C.[C:25](ON=C(C1C=CC=CC=1)C#N)([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26]>O.O1CCOCC1>[C:25]([NH:9][C@H:8]([C:10]([OH:12])=[O:11])[CH2:7][C:6]1[CH:13]=[CH:14][CH:15]=[C:4]([C:2]#[N:3])[CH:5]=1)([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
6 g (26.5 mmol) of 3-cyano-(L)-phenylalanine hydrochloride and 9.1 ml (53.2 mmol) of N-ethyldiisopropylamine was suspended in 17 ml of water. To this suspension was added a solution of 7.2 g (29.2 mmol) of 2-(Boc-oxyimino)-2-phenylacetonitrile in 20 ml of dioxane and stirring continued for 16 hours at room temperature. After subsequent addition of 50 ml of water, the solution was extracted with 50 ml of ethyl acetate, the organic phase separated and the pH of the aqueous phase adjusted to 3 with dilute hydrochloric acid. After 3 extractions with 100 ml each of ethyl acetate, the collected organic solutions were washed with saturated sodium chloride solution, dried over magnesium sulfate and the solvent was evaporated under reduced pressure.
Workup
- extractionthe solution was extracted with 50 ml of ethyl acetate
- customthe organic phase separated
- extractionAfter 3 extractions with 100 ml each of ethyl acetate
- washthe collected organic solutions were washed with saturated sodium chloride solution
- dry with materialdried over magnesium sulfate
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-4299b06c6a314c349529e6e8e8bfb52e
- Source dataset
- uspto-grants-1997_03
- Patent number
- US05607937
Reaction notes
Loading…