Dichloroacetyl chloride → HCID 54567802, 화합물

HRID 1415897노트

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HRID 1415897 반응식
[F:1][C:2]1[CH:3]=[C:4]([N:13]2[CH2:17][C@H:16]([CH2:18][N:19]=[N+]=[N-])[O:15][C:14]2=[O:22])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[CH:11][N:10]=[N:9]1.C(N(CC)CC)C.[Cl:30][CH:31]([Cl:35])[C:32](Cl)=[O:33]>C1COCC1.[Ni].C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([N:13]2[CH2:17][C@H:16]([CH2:18][NH:19][C:32](=[O:33])[CH:31]([Cl:35])[Cl:30])[O:15][C:14]2=[O:22])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[CH:11][N:10]=[N:9]1

참가 물질

7

반응물 3

HCID 6593Dichloroacetyl chlorideHCID 8471TriethylamineHCID 53812503HCID 53812503, 화합물

생성물 1

HCID 54567802HCID 54567802, 화합물수율 52%

시약·촉매·용매 3

HCID 935Nickel촉매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

A solution of 275 mg (0.91 mmol) of (R)-[3-[3-Fluoro-4-(1H-1,2,3-triazol-1-yl)phenyl]-2-oxo-5-oxazolidinyl]methylazide (from Example 6) in 15 mL THF was treated with 1.5 g of W-2 Raney nickel, and hydrogenated at atmospheric pressure. After 18 h, the mixture was filtered through celite, washing the filter cake with methanol. The filtrate was concentrated in vacuo and the resulting oil was slurried in 15 mL methylene chloride, cooled to 0° C. and treated with 138 mg (0.19 mL, 1.36 mmol) triethylamine, and 161 mg (0.11 mL, 1.09 mmol) dichloroacetyl chloride. After stirring at ambient temperature for 24 h, the mixture was diluted with methylene chloride and extracted with water (3×20 mL) and saturated aqueous sodium chloride (1×20 mL). Drying (Na2SO4) and concentration in vacuo afforded an off-white solid. The crude material was subjected to radial chromatography on a 4 mm chromatotron plate eluting with dichloromethane and 2% (v/v) methanol-dichloromethane. These procedures afforded 182 mg (52%) of the title compound as a white solid, mp 195-198° C. dec.

후처리

  1. filtrationthe mixture was filtered through celite
  2. washwashing the filter cake with methanol
  3. concentrationThe filtrate was concentrated in vacuo
  4. extractionextracted with water (3×20 mL) and saturated aqueous sodium chloride (1×20 mL)
  5. customDrying
  6. concentration(Na2SO4) and concentration in vacuo
  7. customafforded an off-white solid
  8. washeluting with dichloromethane and 2% (v/v) methanol-dichloromethane

출처 및 근거

ORD 기록
ord-8340e08c73c2475eb06b9a67fc1ddee8
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05910504

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