Triethylamine → Tert-butyl 3-(4-cyano-2,6-dimethylphenyl)propanoate

HRID 2047297Notes

Reaction equation

HRID 2047297 reaction equation
[C:1]([O:5][C:6](=[O:20])[CH2:7][CH2:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16](=O)[NH2:17])=[CH:11][C:10]=1[CH3:19])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[C:1]([O:5][C:6](=[O:20])[CH2:7][CH2:8][C:9]1[C:10]([CH3:19])=[CH:11][C:12]([C:16]#[N:17])=[CH:13][C:14]=1[CH3:15])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 11849882Tert-butyl 3-(2,6-dimethyl-4-carbamoylphenyl)propanoate

Product 1

HCID 66935544Tert-butyl 3-(4-cyano-2,6-dimethylphenyl)propanoateYield 64.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of 3-(4-carbamoyl-2,6-dimethyl-phenyl)-propionic acid tert-butyl ester (7.00 g, 25.2 mmol) and triethylamine (7.66 g, 75.7 mmol) in DCM (100 mL), trifluoroacetic anhydride (6.06 g, 28.8 mmol) is added slowly so that the reaction temperature stays below 15° C. The clear yellow solution is stirred at rt for 1 h before it is washed twice with water (100 mL) and concentrated. The crude product is purified by recrystallisation from methanol to give 3-(4-cyano-2,6-dimethyl-phenyl)-propionic acid tert-butyl ester (4.2 g) as a white solid, 1H NMR (CDCl3): δ 1.48 (s, 9H), 2.33-2.37 (m, 2H), 2.38 (s, 6H), 2.94-3.01 (m, 2H), 7.31 (s, 2H).

Workup

  1. additionis added slowly so that the reaction temperature
  2. customstays below 15° C
  3. washis washed twice with water (100 mL)
  4. concentrationconcentrated
  5. customThe crude product is purified by recrystallisation from methanol

Sources & evidence

ORD record
ord-a49bd8b3feb84af6be76ce11f8eb6103
Source dataset
uspto-grants-2013_11
Patent number
US08592460B2

Reaction notes

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