Triethylamine → HCID 54191973, compound

HRID 583426Notes

Reaction equation

HRID 583426 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH:5]=[CH:6][CH:7]([NH:21][CH3:22])[CH:8]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:2].[F:24][C:25]([F:40])([F:39])[C:26]1[CH:27]=[C:28]([CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=1)[C:29](Cl)=[O:30].C(N(CC)CC)C>C(Cl)Cl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:23])[CH:5]=[CH:6][CH:7]([N:21]([C:29](=[O:30])[C:28]1[CH:32]=[C:33]([C:35]([F:36])([F:37])[F:38])[CH:34]=[C:26]([C:25]([F:24])([F:39])[F:40])[CH:27]=1)[CH3:22])[CH:8]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:2]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 54455605HCID 54455605, compound

Product 1

HCID 54191973HCID 54191973, compound

Reagents, catalysts & solvents 3

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

Procedure

A solution of 10.6 g (34.3 mmol) of 4-methylamino-5,5-diphenyl-pent-2-enoic acid ethyl ester in 110 ml of methylene chloride is added at 0° C. via a cannula to a solution of 6.7 ml (36.0 mmol) of 3,5-bistrifluoromethyl-benzoyl chloride in 110 ml of methylene chloride. 5.8 ml (41.1 mmol) of triethylamine and 0.4 g (3.4 mmol) of 4-dimethylaminopyridine are then added. After 1 hour the reaction mixture is diluted with ethyl acetate and washed twice with water and once with brine. The aqueous phases are back-extracted once with ethyl acetate. The combined organic phases are then dried over magnesium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel with methylene chloride/methanol (100:0 to 98:2). The title compound is obtained in the form of a light-yellow foam. TLC: methylene chloride/methanol (98:2) Rf =0.38; Rt (HPLC)=22.4 min; 1H-NMR (400 MHz, d6 -DMSO, 120° C.) d 8.00 (br, 1H), 7.47-7.29 (m, 10H), 7.26-7.20 (m, 2H), 6.83 (dd, 1H), 5.96 (d, 1H), 5.89 (br, 1H), 4.65 (d, 1H), 4.10 (q, 2H), 2.68 (s, 3H), 1.18 (t, 3H); FAB-MS (M+H)+ =550.

Workup

  1. washwashed twice with water and once with brine
  2. extractionThe aqueous phases are back-extracted once with ethyl acetate
  3. dry with materialThe combined organic phases are then dried over magnesium sulfate
  4. concentrationconcentrated by evaporation
  5. customThe residue is chromatographed on silica gel with methylene chloride/methanol (100:0 to 98:2)

Sources & evidence

ORD record
ord-3ac8dd103b8d4e4b92aace2aa84b6c21
Source dataset
uspto-grants-1999_07
Patent number
US05929067

Reaction notes

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