Triethylamine → HCID 54447796, compound

HRID 583431Notes

Reaction equation

HRID 583431 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:22])[CH2:5][CH:6]([NH:20][CH3:21])[CH:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[F:23][C:24]([F:39])([F:38])[C:25]1[CH:26]=[C:27]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[C:28](Cl)=[O:29].C(N(CC)CC)C>C(Cl)Cl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[CH3:2][O:3][C:4](=[O:22])[CH2:5][CH:6]([N:20]([C:28](=[O:29])[C:27]1[CH:31]=[C:32]([C:34]([F:35])([F:36])[F:37])[CH:33]=[C:25]([C:24]([F:23])([F:38])[F:39])[CH:26]=1)[CH3:21])[CH:7]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 67563677HCID 67563677, compound

Product 1

HCID 54447796HCID 54447796, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6.8 g (21 mmol) of 3-methylamino-4,4-diphenyl-butanoic acid methyl ester hydrochloride in 100 ml of methylene chloride is added to a solution of 4.2 ml (22 mmol) of 3,5-bistrifluoromethyl-benzoyl chloride in 100 ml of methylene chloride. Then, at 0° C., 6.6 ml (46 mmol) of triethylamine and 0.26 g (2.1 mmol) of 4-dimethylaminopyridine are added. After 6 hours the reaction mixture is diluted with ethyl acetate and washed twice with water and once with brine. The organic phase is dried over sodium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel with methylene chloride/methanol (99:1 to 95:5). The title compound is obtained in the form of a light-yellow solid. TLC: methylene chloride/methanol (95:5) Rf =0.88; Rt (HPLC)=21.4 min; 1H-NMR (400 MHz, d6 -DMSO, 150° C.) d 7.97 (br, 1H), 7.45-7.19 (m, 12H), 5.46 (br, 1H), 4.46 (d, 1H), 3.54 (s, 3H), 2.87 (dd, 1H), 2.72 (s, 3H), 2.47 (dd, 1H); FAB-MS (M+H)+ =524.

Workup

  1. washwashed twice with water and once with brine
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. concentrationconcentrated by evaporation
  4. customThe residue is chromatographed on silica gel with methylene chloride/methanol (99:1 to 95:5)

Sources & evidence

ORD record
ord-ba20bfd937d145d989e53e0bd244716b
Source dataset
uspto-grants-1999_07
Patent number
US05929067

Reaction notes

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