Water → N-benzyl-N-[2-(3,4-dichlorophenyl)-3-ethoxy-3-oxopropyl]-beta-alanine ethyl ester

HRID 1260910Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH2:6][NH:7][CH2:8][CH:9]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.O>C(#N)C>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH2:6][N:7]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:8][CH:9]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:2]

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of the compound (27.8 g) obtained in step 2 and sodium carbonate (16.3 g) in acetonitrile (132 mL) was added benzyl bromide (14.4 g) at room temperature, and the mixture was stirred at 75° C. for 2 hr. The reaction mixture was poured into water, and the resultant product was extracted with ethyl acetate. The organic layer was washed with brine and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 5→20% ethyl acetate/hexane) to give N-benzyl-N-[2-(3,4-dichlorophenyl)-3-ethoxy-3-oxopropyl]-β-alanine ethyl ester (34.6 g, 99%) as a colorless oil.

Workup

extractionthe resultant product was extracted with ethyl acetate
washThe organic layer was washed with brine
customdried
customthe solvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 5→20% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-df46ca8bab8d4b79af72de0cbc037774
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08470816B2

Reaction notes

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