tert-butyl N-(prop-2-yn-1-yl)carbamate → Tert-butyl({1-[(6-bromopyridin-2-yl)methyl]-1h-1,2,3-triazol-4-yl}methyl)carbamate

HRID 386044노트

반응식

HRID 386044 반응식
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[N:6]=1)=[N+:2]=[N-:3].[CH2:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:13]#[CH:14].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CC(O)(C)C.O.C([O-])(O)=O.[Na+]>[C:18]([O:17][C:16](=[O:22])[NH:15][CH2:12][C:13]1[N:3]=[N:2][N:1]([CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[N:6]=2)[CH:14]=1)([CH3:21])([CH3:20])[CH3:19]

참가 물질

7

반응물 3

HCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamateHCID 23667548Sodium AscorbateHCID 453574032-(Azidomethyl)-6-bromopyridine

생성물 1

HCID 59526311Tert-butyl({1-[(6-bromopyridin-2-yl)methyl]-1h-1,2,3-triazol-4-yl}methyl)carbamate

시약·촉매·용매 3

HCID 962Water용매3회HCID 6386tert-Butanol용매HCID 516892Sodium Bicarbonate용매

실험 절차

2-(Azidomethyl)-6-bromopyridine (Example 470 Step 1) (700 mg, 3.29 mmol) and tert-butyl prop-2-yn-1-ylcarbamate (510 mg, 3.29 mmol) were combined in t-BuOH (6.0 mL) and water (3.0 mL). CuSO4.5H2O (41 mg, 0.16 mmol) in water (1.0 mL) was added, followed by sodium ascorbate (130 mg, 0.66 mmol) in water (2.0 mL). The reaction was stirred at room temperature for 2 h. The solution was subsequently diluted with saturated NaHCO3 and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated. Purification by flash chromatography (40-100% EtOAc/hexanes) afforded the title compound as a colorless solid.

후처리

  1. extractionextracted with EtOAc (3×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash chromatography (40-100% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-520ee6de75a6473996841c3bfcdbc32c
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367706B2

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