Acetyl chloride → 2-Acetylamino-3-(4-methoxy-phenyl)-3-oxo-propionic acid methyl ester
Reaction equation
[NH2:1][CH:2]([C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)=[O:8])[C:3]([O:5][CH3:6])=[O:4].CCN(CC)CC.[C:24](Cl)([CH3:26])=[O:25]>C(Cl)Cl>[C:24]([NH:1][CH:2]([C:7]([C:9]1[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1)=[O:8])[C:3]([O:5][CH3:6])=[O:4])(=[O:25])[CH3:26]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
To a solution of methyl 2-amino-3-(4-methoxyphenyl)-3-oxopropanoate (35.5 g, 137 mmol) and Et3N (57.2 mL, 411 mmol) in DCM (120 mL) at 0° C. was added AcCl (12.9 g, 164 mmol) dropwise. The reaction mixture was stirred at 0° C. for 40 min and then quenched with water (500 mL). The resulting mixture was extracted with DCM (300 mL×2) and the combined organic layers were dried over anhydrous sodium sulfate and concentrated. The residue was washed with petroleum ether/EtOAc (300 mL, 100:1) to methyl 2-acetamido-3-(4-methoxyphenyl)-3-oxopropanoate (22.0 g, 61% yield) as a colorless solid.
Workup
- customquenched with water (500 mL)
- extractionThe resulting mixture was extracted with DCM (300 mL×2)
- dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-77d839f7ffb9460ca32efd7a5589432d
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434761B2
Reaction notes
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