Potassium Carbonate → HCID 13300084, compound

HRID 1853385Notes

Reaction equation

HRID 1853385 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([NH:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl[C:22](=[O:30])[CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>O1CCCC1.O>[CH2:7]([N:14]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:22](=[O:30])[CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 80908N-Benzylglycine ethyl esterHCID 84648Butanoic acid, 4-chloro-4-oxo-, ethyl ester

Product 1

HCID 13300084HCID 13300084, compoundYield 85.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Potassium carbonate (110.4 g, 0.97 mol) was added in one portion to a solution of ethyl 2-(benzylamino)acetate (78 g, 0.4 mol) in tetrahydrofuran (500 mL) and water (200 mL). Ethyl 4-chloro-4-oxobutanoate (72.7 g, 0.485 mol) in anhydrous tetrahydrofuran (200 mL) was then added dropwise over a period of 1 hour to the mixture. The mixture was filtered, and the filtrate was washed with ethyl acetate. After the solvent was removed by evaporation, standard extractive workup with ethyl acetate (100 mL) to afford the title product as a yellow oil (110 g; yield=80%). LC-MS: m/z=322 (M+H)+.

Workup

  1. filtrationThe mixture was filtered
  2. washthe filtrate was washed with ethyl acetate
  3. customAfter the solvent was removed by evaporation, standard extractive workup with ethyl acetate (100 mL)

Sources & evidence

ORD record
ord-12e7fca119e7481cadc1524a3434d020
Source dataset
uspto-grants-2015_02
Patent number
US08962638B2

Reaction notes

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