Triethylamine → Tert-butyl (tert-butoxycarbonyl{6-[(pyridin-3-ylsulfonyl)aminomethyl]pyridin-2-yl}amino)acetate

HRID 2359828노트

반응식

HRID 2359828 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7](Cl)(=[O:9])=[O:8])[CH:2]=1.[C:11]([O:15][C:16](=[O:34])[CH2:17][N:18]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][NH2:33])[N:27]=1)[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C.S([O-])(O)(=O)=O.[K+]>C(Cl)Cl>[C:11]([O:15][C:16](=[O:34])[CH2:17][N:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][NH:33][S:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)(=[O:9])=[O:8])[N:27]=1)([CH3:14])([CH3:13])[CH3:12]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 516920Potassium bisulfateHCID 3164136Pyridine-3-sulfonyl chlorideHCID 86651796Tert-butyl [(6-aminomethylpyridin-2-yl)tert-butoxycarbonylamino]acetate

생성물 1

HCID 86651773Tert-butyl (tert-butoxycarbonyl{6-[(pyridin-3-ylsulfonyl)aminomethyl]pyridin-2-yl}amino)acetate수율 85.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 3-pyridylsulfonyl chloride (640 mg, 3.60 mmol) in methylene chloride (14 ml) were added tert-butyl[(6-aminomethylpyridin-2-yl)tert-butoxycarbonylamino]acetate (1.20 g, 3.56 mmol) obtained in Reference Example 12-(c) and triethylamine (2.24 ml, 16.2 mmol), followed by stirring at room temperature for 1 hour. After completion of the reaction, a 5% aqueous potassium hydrogensulfate solution was added to the reaction solution, followed by extraction with chloroform. The separated organic layer was washed sequentially with a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=1:1→1:2 (V/V)), and fractions containing the desired compound were concentrated under reduced pressure to afford the title compound (1.45 g) as a colorless oil. (Yield: 85%)

후처리

  1. customAfter completion of the reaction
  2. extractionfollowed by extraction with chloroform
  3. washThe separated organic layer was washed sequentially with a saturated aqueous sodium hydrogencarbonate solution
  4. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additioncontaining the desired compound
  7. concentrationwere concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-f45d09c90c174f16bd670c50e92401ac
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08685986B2

반응 노트

불러오는 중…