Aminoisobutyric acid → HCID 53491902, compound

HRID 2045336Notes

Reaction equation

HRID 2045336 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([Cl:24])[CH:8]=[C:9]2[C:14]=1[NH:13][CH:12]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17](Br)[CH:16]=1)[C:11]([CH3:23])([CH3:22])[CH2:10]2)=[O:4].[NH2:25][C:26]([CH3:31])([CH3:30])[C:27]([OH:29])=[O:28].Cl.CN(C)CC(O)=O.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu]I.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([Cl:24])[CH:8]=[C:9]2[C:14]=1[NH:13][CH:12]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:25][C:26]([C:27]([OH:29])=[O:28])([CH3:31])[CH3:30])[CH:16]=1)[C:11]([CH3:23])([CH3:22])[CH2:10]2)=[O:4]

Participants

8

Reactant 4

HCID 6119Aminoisobutyric acidHCID 11430Potassium CarbonateHCID 75605N,N-Dimethylglycine hydrochlorideHCID 674420582-(3-Bromo-phenyl)-6-chloro-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester

Product 1

HCID 53491902HCID 53491902, compoundYield 24%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-(3-bromo-phenyl)-6-chloro-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester (1.2 g, 2.94 mmol), 2-aminoisobutyric acid (1.20 g, 12 mmol), copper (I) iodide (0.34 g, 1.76 mmol), N,N-dimethylglycine hydrochloride (0.33 g, 2.35 mmol) and potassium carbonate (1.22, 8.82 mmol) in DMSO (10 mL) was heated for 4 hours at 120° C. After cooling to room temperature, the mixture was treated with ethyl acetate (50 mL) and washed with water (20 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% formic acid in water) afforded 2-[3-(1-carboxy-1-methyl-ethylamino)-phenyl]-6-chloro-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester (300 mg, 24%) as a white solid: LC/MS m/e calcd for C23H27ClN2O4 (M+H)+: 431.9, observed: 431.1.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water (20 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% formic acid in water)

Sources & evidence

ORD record
ord-7fba354ca3584cd0a047420d6116c60c
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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