Phenylacetic Acid → HCID 67443648, compound

HRID 1801207Notes

Reaction equation

HRID 1801207 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[NH3+].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[CH2:51]([O:53][C:54]([C:56]1[CH:57]=[C:58]2[C:63](=[CH:64][CH:65]=1)[NH:62][CH:61]([C:66]1[CH:71]=[CH:70][CH:69]=[C:68]([NH2:72])[CH:67]=1)[C:60]([CH3:74])([CH3:73])[CH2:59]2)=[O:55])[CH3:52]>ClCCl>[CH2:51]([O:53][C:54]([C:56]1[CH:57]=[C:58]2[C:63](=[CH:64][CH:65]=1)[NH:62][CH:61]([C:66]1[CH:71]=[CH:70][CH:69]=[C:68]([NH:72][C:8](=[O:10])[CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:67]=1)[C:60]([CH3:73])([CH3:74])[CH2:59]2)=[O:55])[CH3:52]

Participants

6

Reactant 4

HCID 999Phenylacetic AcidHCID 8471TriethylamineHCID 674427962-(3-Amino-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl esterHCID 866211442-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate Methanaminium

Product 1

HCID 67443648HCID 67443648, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of phenylacetic acid (850 mg, 6.2 mmol), 2-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate Methanaminium (HATU) (3.5 g, 9.3 mmol) and triethyl amine (2.6 mL, 18.6 mmol) in dichloromethane (20 mL) was added 2-(3-amino-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (2.0 g, 6.2 mmol) at room temperature and stirred at room temperature for overnight. Then the reaction mixture was concentrated in vacuo and the residue was extracted with ethyl acetate (2×200 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 3,3-dimethyl-2-(3-phenylacetylamino-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (2.7 g, quant.) as a light yellow solid which was used for next step without further purification: LC/MS m/e calcd for C28H30N2O3 (M+H)+: 443.56, observed: 443.1.

Workup

  1. concentrationThen the reaction mixture was concentrated in vacuo
  2. extractionthe residue was extracted with ethyl acetate (2×200 mL)
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9be840c7dfd7420490aaf05f3c881867
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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