Hydrochloric Acid → Methyl 2-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-4-pentenoate
Reaction equation
[CH:1](NC(C)C)([CH3:3])[CH3:2].C([Li])CCC.[CH3:13][O:14][C:15](=[O:26])[CH2:16][CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C(Br)C=C.Cl>O1CCCC1.CCCCCC>[C:22]([O:21][C:19]([NH:18][CH2:17][CH:16]([CH2:3][CH:1]=[CH2:2])[C:15]([O:14][CH3:13])=[O:26])=[O:20])([CH3:23])([CH3:25])[CH3:24]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
Dissolve diisopropylamine (5.6 mL, 40 mmol) in anhydrous tetrahydrofuran, cool to -78° C. and place under nitrogen atmosphere. Treat with n-butyllithium (25 mL of a 1.6M solution in hexane, 40 mmol). Stir for 30 minutes and add, by dropwise addition, a solution of N-(t-butyloxycarbonyl)-β-alanine methyl ester (4.06 g, 20 mmol) in tetrahydrofuran (25 mL) over 20 minutes. Stir for an additional 30 minutes. Add allyl bromide (1.72 mL, 20 mmol) and allow the mixture to warm to room temperature with stirring until homogeneous. Cool to -78° C. and slowly warm to -20° C. over 30 minutes. Pour into 5% hydrochloric acid, extract into ether, wash with saturated sodium chloride, dry, and concentrate to yield 5.01 g yellow oil. Purify by silica gel chromatography (25% ethyl acetate/hexane) to yield 4.2 g (87%) of a racemic mixture of the title compound as a clear colorless oil.
Workup
- additionadd, by dropwise addition
- stirringStir for an additional 30 minutes
- temperatureto warm to room temperature
- stirringwith stirring until homogeneous
- temperatureCool to -78° C.
- temperatureslowly warm to -20° C. over 30 minutes
- extractionextract into ether
- washwash with saturated sodium chloride
- customdry
- concentrationconcentrate
Sources & evidence
- ORD record
- ord-d9107d4a61cf45859ebbada70744d2c7
- Source dataset
- uspto-grants-1996_06
- Patent number
- US05527795
Reaction notes
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