Trifluoroacetic acid → Methyl 3,5-dichloro-4-(2-pyrrolidinyl)methoxybenzoate

HRID 354293노트

반응식

HRID 354293 반응식
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][O:14][C:15]1[C:24]([Cl:25])=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][C:16]=1[Cl:26])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:26][C:16]1[CH:17]=[C:18]([CH:23]=[C:24]([Cl:25])[C:15]=1[O:14][CH2:13][CH:9]1[CH2:10][CH2:11][CH2:12][NH:8]1)[C:19]([O:21][CH3:22])=[O:20]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 23511702Methyl 4-[1-(tert-butoxycarbonyl)-2-pyrrolidinyl]methoxy-3,5-dichlorobenzoate

생성물 1

HCID 23512157Methyl 3,5-dichloro-4-(2-pyrrolidinyl)methoxybenzoate수율 68%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of methyl 4-[1-(tert-butoxycarbonyl)-2-pyrrolidinyl]methoxy-3,5-dichlorobenzoate (988 mg, 3.248 mmol) in CH2Cl2 (20 mL) was added TFA (5 mL) at 0° C., and the reaction mixture was stirred at room temp for 2 hr. The solvent was removed under a reduced pressure and the residue was treated with 1N NaOH. The solution was extracted with CHCl3. The extract was washed with brine, dried over Na2SO4, and concentrated under a reduced pressure to afford 672 mg (68%) methyl 3,5-dichloro-4-(2-pyrrolidinyl)methoxybenzoate as a pale yellowish oil. 1H-NMR (400 MHz, CDCl3) δ1.62-1.69 (m, 1H), 1.78-1.86 (m, 2H), 1.89-199 (m, 1H), 2.92-2.98 (m, 1H), 3.04-3.09 (m, 1H), 3.55-3.60 (m, 1H), 3.91 (s, 3H), 4.01 (dd, J=6.8, 8.8 Hz, 1H), 4.08 (dd, J=4.9, 8.8 Hz, 1H), 7.97 (s, 2H); MS (FAB) m/z 304 (M++1).

후처리

  1. customThe solvent was removed under a reduced pressure
  2. additionthe residue was treated with 1N NaOH
  3. extractionThe solution was extracted with CHCl3
  4. washThe extract was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under a reduced pressure

출처 및 근거

ORD 기록
ord-5cfa8d6fe7cb458a93b2ff2f8f59338c
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756378B2

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