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Trifluoroacetic acid → Diethyl 1-(4-aminobutan-2-yl)-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate

HRID 1521709
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HRID 1521709 반응식
C(OC([NH:8][CH2:9][CH2:10][CH:11]([N:13]1[C:17]2=[N:18][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:21]=[C:16]2[CH:15]=[C:14]1[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH3:12])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][CH2:9][CH2:10][CH:11]([N:13]1[C:17]2=[N:18][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:21]=[C:16]2[CH:15]=[C:14]1[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH3:12]
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반응물 2

HCID 6422Trifluoroacetic acidHCID 67238426HCID 67238426, 화합물

생성물 1

HCID 67237898Diethyl 1-(4-aminobutan-2-yl)-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate수율 129.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of diethyl 1-{4-[(tert-butoxycarbonyl)amino]butan-2-yl}-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate (1.20 g, 2.77 mmol) in CH2Cl2 (16 mL) is added TFA (4 mL). The mixture is stirred at room temperature for 3 hr. The mixture is concentrated under reduced pressure 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 (1.20 g, >99%) which is used in the next step without purification. LCMS: 334.75 (M+H+).

후처리

  1. concentrationThe mixture is concentrated under reduced pressure
  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-5d6d9a8074e84a3f8b15f7ed98b58041
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09073926B2

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