Ammonia → Tert-butyl 3-(2,6-dimethyl-4-carbamoylphenyl)propanoate

HRID 2037352노트

반응식

HRID 2037352 반응식
[C:1]([O:5][C:6]([CH2:8][CH2:9][C:10]1[C:18]([CH3:19])=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][C:11]=1[CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=[N:27]C=2C=1.CCN=C=NCCCN(C)C.Cl.N>C(O)(C)C>[C:1]([O:5][C:6](=[O:7])[CH2:8][CH2:9][C:10]1[C:18]([CH3:19])=[CH:17][C:13]([C:14](=[O:15])[NH2:27])=[CH:12][C:11]=1[CH3:20])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 594979324-(2-Tert-butoxycarbonyl-ethyl)-3,5-dimethyl-benzoic acid

생성물 1

HCID 11849882Tert-butyl 3-(2,6-dimethyl-4-carbamoylphenyl)propanoate수율 94.2%

시약·촉매·용매 1

HCID 3776Isopropanol용매2회

실험 절차

To a suspension of 4-(2-tert-butoxycarbonyl-ethyl)-3,5-dimethyl-benzoic acid (8.00 g, 28.7 mmol) in isopropanol (100 mL), HOBt (4.27 g, 31.6 mmol) followed by EDC hydrochloride (6.34 g, 33.1 mmol) is added. After stirring at rt for 1 h, 25% aq. ammonia (16.1 mL) is added. Stirring is continued for 30 min before the isopropanol is evaporated under reduced pressure. The remaining solution is diluted with isopropyl acetate (200 mL), washed three times with approximately 0.5 N aq. NaHCO3 solution (100 mL) followed by water (50 mL), dried over MgSO4, filtered, concentrated and dried to give 3-(4-carbamoyl-2,6-dimethyl-phenyl)-propionic acid tert-butyl ester (7.5 g) as an off-white solid.

후처리

  1. additionis added
  2. stirringStirring
  3. customis evaporated under reduced pressure
  4. additionThe remaining solution is diluted with isopropyl acetate (200 mL)
  5. washwashed three times with approximately 0.5 N aq. NaHCO3 solution (100 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customdried

출처 및 근거

ORD 기록
ord-e433909f4eef40978179ba6401164e03
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575200B2

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