5-Chloro-1H-indole-2-carboxylic acid → HCID 54395516, compound

HRID 651163Notes

Reaction equation

HRID 651163 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]([NH2:13])([CH3:12])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([C:25](O)=[O:26])=[CH:19]2>ClCCl.CN(C)C=O>[CH3:1][O:2][C:3](=[O:14])[C:4]([NH:13][C:25]([C:20]1[NH:21][C:22]2[C:18]([CH:19]=1)=[CH:17][C:16]([Cl:15])=[CH:24][CH:23]=2)=[O:26])([CH3:12])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 568302Methyl 2-amino-2-methyl-3-phenylpropanoate

Product 1

HCID 54395516HCID 54395516, compound

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

Racemic 2-amino-2-methyl-3-phenyl-propionic acid methyl ester (200 mg, 0.87 mmol) and 5-chloro-1H-indole-2-carboxylic acid (170 mg, 0.87 mmol) were coupled according to Procedure A (2:1 dichloromethane/dimethylformamide solvent) and the product purified by chromatography on silica gel eluted with 10% ethyl acetate in hexanes. Yield 286 mg, 89%; HPLC (60/40) 9.63 minutes (85%); TSPMS 371/373 (MH+, 100%);

Workup

  1. customthe product purified by chromatography on silica gel
  2. washeluted with 10% ethyl acetate in hexanes
  3. customHPLC (60/40) 9.63 minutes (85%)

Sources & evidence

ORD record
ord-ee0e6ae6234b466aad05cbea59c28c65
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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