4-Methylmorpholine → (S)-tert-Butyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate
Reaction equation
[NH:1]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:2]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3][C:4](=O)[OH:5].CN1CCOCC1.ClC(OCC(C)C)=O.[BH4-].[Na+]>COCCOC.O>[C:17]([O:16][C:14]([NH:1][C@H:2]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3][CH2:4][OH:5])=[O:15])([CH3:19])([CH3:20])[CH3:18]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -15 °C
Procedure
To a solution of Boc-L-Asp-OtBu (3.00 g, 10.4 mmol) in 1,2-dimethoxyethane (10 mL) was added at −15° C. 4-methylmorpholine (1.14 mL, 10.4 mmol) and isobutyl chloroformate (1.35 mL, 10.4 mmol). After stirring for 10 min at −15° C. the precipitate was filtered off and washed with cold 1,2-dimethoxyethane (20 mL). To the filtrate was added at −15° C. a solution of sodium borohydride (0.59 g, 15.6 mmol) in water (5 mL). After 5 min water (250 mL) was added. The reaction mixture was extracted with ethyl acetate (3×100 mL), the combined organic layers dried over sodium sulphate, and concentrated under reduced pressure to give the title compound.
Workup
- filtrationwas filtered off
- washwashed with cold 1,2-dimethoxyethane (20 mL)
- extractionThe reaction mixture was extracted with ethyl acetate (3×100 mL)
- dry with materialthe combined organic layers dried over sodium sulphate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-98c7d20b18214bd995fd50667892be43
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09017645B2
Reaction notes
Loading…