tert-Butyl acetate → Di-tert-butyl (R)-2-aminopentanedioate
Reaction equation
[NH2:1][C@@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].Cl(O)(=O)(=O)=O.C(O[C:20]([CH3:23])([CH3:22])[CH3:21])(=O)C>>[C:20]([O:9][C:8](=[O:10])[C@@H:2]([CH2:3][CH2:4][C:5]([O:7][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:6])[NH2:1])([CH3:23])([CH3:22])[CH3:21]Participants
4
Procedure
D-Glutamic acid (5.88 g), tert-butyl acetate (100 ml) and 70% aqueous perchloric acid (6.3 g) were stirred at laboratory temperature for 4 days. The mixture was then cooled in an ice-water bath and extracted with 0.5 N hydrochloric acid (3×100 ml). The combined aqueous extracts were immediately neutralised with solid sodium bicarbonate. The aqueous solution was extracted with diethyl ether (3×100 ml), the ether extracts pooled, dried over anhydrous sodium sulphate and the ether evaporated in vacuo to give di-tert-butyl-D-glutamate (0.855 g).
Workup
- temperatureThe mixture was then cooled in an ice-water bath
- extractionextracted with 0.5 N hydrochloric acid (3×100 ml)
- extractionThe aqueous solution was extracted with diethyl ether (3×100 ml)
- dry with materialdried over anhydrous sodium sulphate
- customthe ether evaporated in vacuo
Sources & evidence
- ORD record
- ord-2b18e81db2a14e94a62fea660052f633
- Source dataset
- uspto-grants-1995_08
- Patent number
- US05444061
Reaction notes
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