Pentafluoropropionic acid → HCID 22341386、化合物

HRID 1368364

反応式

HRID 1368364 の反応式
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

参加物

4

反応物 2

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

生成物 1

HCID 22341386HCID 22341386、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-115fbe544f9945749dd974e2db9e3848
出典データセット
uspto-grants-2003_06
特許番号
US06573283B2

関連ノート

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