1-Aminocyclopropane-1-carboxylic acid → HCID 56966639, compound

HRID 1036866Notes

Reaction equation

HRID 1036866 reaction equation
C[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)[CH2:11][C:10]2([CH3:23])[CH3:22])=[O:4].[NH2:25][C:26]1([C:29]([OH:31])=[O:30])[CH2:28][CH2:27]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu]I>[C:29]([C:26]1([NH:25][C:17]2[CH:16]=[C:15]([CH:12]3[CH2:11][C:10]([CH3:22])([CH3:23])[C:9]4[C:14](=[C:5]([C:3]([OH:2])=[O:4])[CH:6]=[C:7]([Cl:24])[CH:8]=4)[NH:13]3)[CH:20]=[CH:19][CH:18]=2)[CH2:28][CH2:27]1)([OH:31])=[O:30]

Participants

6

Reactant 3

HCID 5351-Aminocyclopropane-1-carboxylic acidHCID 11430Potassium CarbonateHCID 67291316HCID 67291316, compound

Product 1

HCID 56966639HCID 56966639, compoundYield 31.5%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2-(3-bromo-phenyl)-6-chloro-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester (408.0 mg, 1.0 mmol), copper(I) iodide (57.0 mg, 0.3 mmol), 1-amino-cyclopropanecarboxylic acid (309.0 mg, 3.0 mmol) and potassium carbonate (415.0 mg, 3.0 mmol) in dimethyl sulfoxide (2.0 mL) was stirred at 120° C. for 16 h. Then the reaction mixture was cooled to room temperature and extracted with ethyl acetate (150 mL×2), washed with water (50 mL×2) and saturated aqueous ammonium chloride solution (50 mL×2), dried over anhydrous sodium sulfate and then 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% ammonium hydroxide in water) afforded 2-[3-(1-carboxy-cyclopropylamino)-phenyl]-6-chloro-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid (130.4 mg, 31.5%) as a white solid: LC/MS m/e obsd. (ESI+) [(M+H)+] 415.1.

Workup

  1. extractionextracted with ethyl acetate (150 mL×2)
  2. washwashed with water (50 mL×2) and saturated aqueous ammonium chloride solution (50 mL×2)
  3. dry with materialdried 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% ammonium hydroxide in water)

Sources & evidence

ORD record
ord-a64a3d3c86934a2dbac8117d502bbe3d
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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