Trifluoroacetic acid → Diethyl 1-(3-amino-2,2-dimethylpropyl)-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate

HRID 1521704노트

반응식

HRID 1521704 반응식
C(OC([NH:8][CH2:9][C:10]([CH3:32])([CH3:31])[CH2:11][N:12]1[C:16]2=[N:17][C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:20]=[C:15]2[CH:14]=[C:13]1[C:26]([O:28][CH2:29][CH3:30])=[O:27])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][CH2:9][C:10]([CH3:31])([CH3:32])[CH2:11][N:12]1[C:16]2=[N:17][C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:20]=[C:15]2[CH:14]=[C:13]1[C:26]([O:28][CH2:29][CH3:30])=[O:27]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 67238212Diethyl 1-{3-[(tert-butoxycarbonyl)amino]-2,2-dimethylpropyl}-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate

생성물 1

HCID 67237221Diethyl 1-(3-amino-2,2-dimethylpropyl)-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate수율 101.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of diethyl 1-{3-[(tert-butoxycarbonyl)amino]-2,2-dimethylpropyl}-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate (4.20 g, 9.39 mmol) in CH2Cl2 (20 mL) is added TFA (10 mL). The mixture is stirred at room temperature for 4 hr. The solvent is evaporated and the residue is partitioned between ethyl acetate and saturated NaHCO3 solution. The layers are separated and the aqueous layer is further extracted with ethyl acetate. The combined organic phases are washed with brine, and are dried (Na2SO4) and concentrated in vacuo to afford the title compound (3.30 g, quantitative). LCMS: 348.79 (M+H+).

후처리

  1. customThe solvent is evaporated
  2. customthe residue is partitioned between ethyl acetate and saturated NaHCO3 solution
  3. customThe layers are separated
  4. extractionthe aqueous layer is further extracted with ethyl acetate
  5. washThe combined organic phases are washed with brine
  6. dry with materialare dried (Na2SO4)
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-91e299f017ff47199f02ae073b4f40b9
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073926B2

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