1-Aminocyclopropane-1-carboxylic acid → HCID 56966638, compound

HRID 1036864Notes

Reaction equation

HRID 1036864 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][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].[NH2:24][C:25]1([C:28]([OH:30])=[O:29])[CH2:27][CH2:26]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu]I>[C:28]([C:25]1([NH:24][C:17]2[CH:16]=[C:15]([CH:12]3[CH2:11][C:10]([CH3:23])([CH3:22])[C:9]4[C:14](=[C:5]([C:3]([OH:2])=[O:4])[CH:6]=[CH:7][CH:8]=4)[NH:13]3)[CH:20]=[CH:19][CH:18]=2)[CH2:27][CH2:26]1)([OH:30])=[O:29]

Participants

6

Reactant 3

HCID 5351-Aminocyclopropane-1-carboxylic acidHCID 11430Potassium CarbonateHCID 67291951HCID 67291951, compound

Product 1

HCID 56966638HCID 56966638, compoundYield 60%

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)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester (374 mg, 1.0 mmol), copper(I) iodide (57 mg, 0.3 mmol), 1-amino-cyclopropanecarboxylic acid (309 mg, 3.0 mmol) and potassium carbonate (415 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]-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid (228 mg, 60.0%) as a white solid: LC/MS m/e obsd. (ESI+) [(M+H)+] 381.0.

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-7aad11bc40a14e889946fd421a8d4824
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

Loading…