Acetic acid, azido-, ethyl ester → Ethyl{4-[(6-bromopyridin-2-yl)(hydroxy)methyl]-1h-1,2,3-triazol-1-yl}acetate

HRID 386075노트

반응식

HRID 386075 반응식
[Br:1][C:2]1[N:7]=[C:6]([CH:8]([OH:11])[C:9]#[CH:10])[CH:5]=[CH:4][CH:3]=1.[N:12]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N+:13]=[N-:14].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CC(O)(C)C.O.C([O-])(O)=O.[Na+]>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][N:12]1[CH:10]=[C:9]([CH:8]([C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=2)[OH:11])[N:14]=[N:13]1)[CH3:20]

참가 물질

7

반응물 3

HCID 69480Acetic acid, azido-, ethyl esterHCID 23667548Sodium AscorbateHCID 595262091-(6-Bromopyridin-2-yl)prop-2-yn-1-ol

생성물 1

HCID 59525849Ethyl{4-[(6-bromopyridin-2-yl)(hydroxy)methyl]-1h-1,2,3-triazol-1-yl}acetate

시약·촉매·용매 3

HCID 962Water용매3회HCID 6386tert-Butanol용매HCID 516892Sodium Bicarbonate용매

실험 절차

1-(6-Bromopyridin-2-yl)prop-2-yn-1-ol (Example 512, Step 1) (500 mg, 2.36 mmol) and ethyl azidoacetate (1.46 mL, 2.59 mmol) were combined in t-BuOH (5.0 mL) and water (3.0 mL). CuSO4.5H2O (29 mg, 0.12 mmol) in water (1.0 mL) was added, followed by sodium ascorbate (93 mg, 0.47 mmol) in water (1.0 mL). The reaction was stirred at room temperature overnight, diluted with saturated NaHCO3, and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated. Purification by flash chromatography (50-100% EtOAc/hexanes) afforded the title compound as a colorless solid.

후처리

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash chromatography (50-100% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-7c658ff8d0dc4774bd07ff008493a00e
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367706B2

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