Benzyl Bromide → HCID 54085496, compound
Reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][OH:14])[CH:10]([CH3:12])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CC(C)([O-])C.[K+]>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:10]([CH3:11])[CH3:12])=[O:7])([CH3:3])([CH3:4])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of N-tert-butoxycarbonyl-(D)-valinol (10 g, 49.3 mmol) and benzylbromide (5.86 ml, 49.3 mmol) in anhydrous DMF (50 ml) was added at -5° C. and under nitrogen, potassium-tert-butoxide (11.06 g, 98.6 mmol) as a solid, portionwise, and in such a way that the internal temperature does not exceed +5° C. The reaction mixture was stirred for 2 hours at 0° C., diluted with ethyl acetate (2×300 ml), extracted with a 1N solution of potassium hydrogenosulfate (50 ml) and water (250 ml) and washed twice with water (2×200 ml). After drying of the organic phase on sodium sulfate, filtration and concentration in vacuo, the resulting oil was purified by flash chromatography (silica gel, ethyl acetate/petroleum ether: 1/9, Rf.: 0.42) to give the title compound as a colorless oil (9.95 g, 69% yield).
Workup
- customdoes not exceed +5° C
- extractionextracted with a 1N solution of potassium hydrogenosulfate (50 ml) and water (250 ml)
- washwashed twice with water (2×200 ml)
- customAfter drying of the organic phase on sodium sulfate, filtration and concentration in vacuo
- customthe resulting oil was purified by flash chromatography (silica gel, ethyl acetate/petroleum ether: 1/9, Rf.: 0.42)
Sources & evidence
- ORD record
- ord-45872abc88fb4c92b2d621947875f088
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05717093
Reaction notes
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