Triethylamine → 3-(4-Cyano-2-ethyl-6-methylphenyl)propionic acid tert-butyl ester

HRID 2040805Notes

Reaction equation

HRID 2040805 reaction equation
[C:1]([O:5][C:6](=[O:21])[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[CH2:19][CH3:20])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[C:1]([O:5][C:6](=[O:21])[CH2:7][CH2:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]#[N:17])=[CH:11][C:10]=1[CH2:19][CH3:20])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 685531653-(4-Carbamoyl-2-ethyl-6-methylphenyl)propionic acid tert-butyl ester

Product 1

HCID 685503513-(4-Cyano-2-ethyl-6-methylphenyl)propionic acid tert-butyl esterYield 100.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-carbamoyl-2-ethyl-6-methyl-phenyl)-propionic acid tert-butyl ester (30.0 g, 103 mmol) and NEt3 (31.3 g, 309 mmol) in DCM (300 mL), trifluoroacetic anhydride (23.8 g, 113 mmol) is added slowly. The exothermic reaction is kept below 5° C. with cooling. After complete addition, the mixture is stirred at rt for 1 h. The mixture is washed twice with water (2×300 mL) and the org. extract is evaporated to dryness to give 3-(4-cyano-2-ethyl-6-methyl-phenyl)-propionic acid tert-butyl ester (28.4 g) as a pale yellow oil; 1H NMR δ 1.25 (t, J=7.5 Hz, 3 H), 1.48 (s, 9 H), 2.32-2.37 (m, 2 H), 2.38 (s, 3 H), 2.70 (q, J=7.5 Hz, 2 H), 2.95-3.02 (m, 2 H), 7.30 (s, 1 H), 7.34 (s, 1 H).

Workup

  1. customThe exothermic reaction
  2. customis kept below 5° C.
  3. temperaturewith cooling
  4. additionAfter complete addition
  5. washThe mixture is washed twice with water (2×300 mL)
  6. extractionextract
  7. customis evaporated to dryness

Sources & evidence

ORD record
ord-3e18c76e047146219449170c9f8837b5
Source dataset
uspto-grants-2013_11
Patent number
US08580824B2

Reaction notes

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