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

HRID 2037353노트

반응식

HRID 2037353 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d8d1536fbfca487f8f4f724d2bf0dac6
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575200B2

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