Pentafluoropropionic acid → HCID 22341386, 화합물

HRID 1368364

반응식

HRID 1368364 반응식
Cl.Cl.[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([O:13][CH2:14][C@@H:15]2[O:20][C:19]3[C:21]([NH2:26])=[C:22]([NH2:25])[CH:23]=[CH:24][C:18]=3[O:17][CH2:16]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1.[F:27][C:28]([F:36])([F:35])[C:29]([F:34])([F:33])[C:30](O)=O>C(Cl)Cl>[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([O:13][CH2:14][CH:15]2[O:20][C:19]3[C:18](=[CH:24][CH:23]=[C:22]4[NH:25][C:30]([C:29]([F:34])([F:33])[C:28]([F:36])([F:35])[F:27])=[N:26][C:21]4=3)[O:17][CH2:16]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1

참가 물질

4

반응물 2

HCID 62356Pentafluoropropionic acidHCID 86586513[(2R)-7,8-diamino-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate dihydrochloride

생성물 1

HCID 22341386HCID 22341386, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 1.0 g (2.4 mmole) of [(2R)-7,8-diamino-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate dihydrochloride in 30 mL of pentafluoropropionic acid was refluxed under nitrogen for 6 hours. The mixture was diluted to 400 mL with methylene chloride, washed with 400 mL of water and with 400 mL of saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered and concentrated to a crude foam in vacuum. The crude product was column chromatographed on silica gel with 1% methanol in chloroform and the product fractions combined and concentrated in vacuum to give 0.90 g of the (R)-enantiomer of the title compound as a yellow oil. 1H-NMR (CDCl3): doublet 7.75 δ(2H); doublet 7.3 δ(2H); doublet 7.15 δ(1H); doublet 6.9 δ(1H); multiplet 4.5 δ(1h); doublet of doublets 4.25 δ(1H); multiplet 4.2 δ(2H); doublet of doublets 4.1 δ(1H); singlet 2.4 δ(3H).

후처리

  1. washwashed with 400 mL of water and with 400 mL of saturated aqueous sodium bicarbonate
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to a crude foam in vacuum
  5. customchromatographed on silica gel with 1% methanol in chloroform
  6. concentrationconcentrated in vacuum

출처 및 근거

ORD 기록
ord-115fbe544f9945749dd974e2db9e3848
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06573283B2

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