Potassium Carbonate → 2-[2-(2,5-Dimethyl-phenyl)-acetylamino]-3-(1-methoxy-piperidin-4-yl)-propionic acid methyl ester

HRID 1844662Notes

Reaction equation

HRID 1844662 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH2:9][C:10](Cl)=[O:11].[CH3:13][O:14][C:15](=[O:27])[CH:16]([NH2:26])[CH2:17][CH:18]1[CH2:23][CH2:22][N:21]([O:24][CH3:25])[CH2:20][CH2:19]1.C([O-])([O-])=O.[K+].[K+]>C1COCC1.O>[CH3:13][O:14][C:15](=[O:27])[CH:16]([NH:26][C:10](=[O:11])[CH2:9][C:3]1[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=1[CH3:1])[CH2:17][CH:18]1[CH2:19][CH2:20][N:21]([O:24][CH3:25])[CH2:22][CH2:23]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 22561615(2,5-Dimethylphenyl)acetyl chlorideHCID 682992242-Amino-3-(1-methoxy-piperidin-4-yl)-propionic acid methyl ester

Product 1

HCID 682992292-[2-(2,5-Dimethyl-phenyl)-acetylamino]-3-(1-methoxy-piperidin-4-yl)-propionic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2,5-Dimethylphenylacetyl chloride (2.1 g, 11.5 mmol) was added dropwise to a mixture of 2-amino-3-(1-methoxy-piperidin-4-yl)-propionic acid methyl ester (1.7 g, 7.8 mmol) and K2CO3 (2.1 g, 15.2 mmol) in 50 mL of THF at room temperature. After the addition, the mixture was stirred for 0.5 h and diluted with 50 ml of water. The mixture was extracted with EtOAc five times and the combined organic layers were dried over sodium sulfate, filtered and concentrated under vacuum. The residue was purified by column chromatography on silica gel. Yield: 1.2 g of 2-[2-(2,5-dimethyl-phenyl)-acetylamino]-3-(1-methoxy-piperidin-4-yl)-propionic acid methyl ester as a solid.

Workup

  1. additionAfter the addition
  2. extractionThe mixture was extracted with EtOAc five times
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-3ec90ee4080e472da3754ad0d577349a
Source dataset
uspto-grants-2015_02
Patent number
US08946453B2

Reaction notes

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