Acetyl chloride → Ethyl (R)-4-Azido-3-Acetoxybutyrate
Reaction equation
[N:1]([CH2:4][C@H:5]([OH:12])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N+:2]=[N-:3].C(N(CC)CC)C.[O:20]1CC[CH2:22][CH2:21]1.C(Cl)(=O)C>CN(C)C1C=CN=CC=1.C(OCC)(=O)C.CCCCCC>[N:1]([CH2:4][C@H:5]([O:12][C:21](=[O:20])[CH3:22])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N+:2]=[N-:3]Participants
7
Conditions
- Temperature
- 0 °C
Procedure
In a 100 ml four-necked flask were charged 5.0 g (28.8 mmol) of ethyl (R)-4-azido-3-hydroxybutyrate, 3.5 g (34.6 mmol) of triethylamine, 0.11 g (0.900 mmol) of 4-dimethylaminopyridine and 50 ml of tetrahydrofuran, and after the mixture was cooled to 0° C., 2.50 g (31.8 mmol) of acetyl chloride was slowly added thereto dropwise in a nitrogen stream. After the addition, the reaction mixture was further stirred at room temperature overnight, and then the solvent was distilled under reduced pressure to give 4.94 g of a concentrate. The concentrate was subjected to column chromatography (ethyl acetate/hexane=1/10 by volume) to obtain 4.50 g (73%) of the title compound.
Workup
- additionAfter the addition
- distillationthe solvent was distilled under reduced pressure
- customto give 4.94 g of a concentrate
Sources & evidence
- ORD record
- ord-70a04e990fb249febcb954f9b795f8ba
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06403804B1
Reaction notes
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