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Pyrrolidine → HCID 70559553, 화합물

HRID 1503846
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HRID 1503846 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:12][C:13]([OH:15])=O)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].[NH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1.C(N(C(C)C)CC)(C)C>S(Cl)(Cl)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:12][C:13]([N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:15])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 16755859(3-Methoxy-4-nitrophenyl)acetic acid

생성물 1

HCID 70559553HCID 70559553, 화합물

시약·촉매·용매 1

HCID 24386Thionyl Chloride용매

실험 절차

A solution of the product of EXAMPLE 30B (1 g, 4.74 mmol) in thionyl dichloride (20 mL) was stirred at reflux for 3 hours. The solution was concentrated and the residue was diluted with dry dichloromethane (20 mL) and dropped into a solution of pyrrolidine (0.63 mL, 7.1 mmol) and diisopropyl ethylamine (1.7 mL, 9.5 mmol). The mixture was stirred at room temperature overnight and the mixture was washed with 1N aqueous hydrochloric acid (20 mL) and brine. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated and the residue was purified by flash chromatography on silica gel eluting with 1/100 methanol/dichloromethane to give the title compound.

후처리

  1. temperatureat reflux for 3 hours
  2. concentrationThe solution was concentrated
  3. additionthe residue was diluted with dry dichloromethane (20 mL)
  4. washthe mixture was washed with 1N aqueous hydrochloric acid (20 mL) and brine
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe residue was purified by flash chromatography on silica gel eluting with 1/100 methanol/dichloromethane

출처 및 근거

ORD 기록
ord-64f33495a64e44f787eb1e9a806fbc8c
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09212192B2

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