Pentafluoropropionic acid → HCID 22341386, compound

HRID 584602

Reaction equation

HRID 584602 reaction equation
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

Participants

4

Reactant 2

HCID 62356Pentafluoropropionic acidHCID 86586513HCID 86586513, compound

Product 1

HCID 22341386HCID 22341386, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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 (2 H); 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 (1 H); singlet 2.4 δ (3H).

Workup

  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

Sources & evidence

ORD record
ord-db768b815f0149d78ee3a8862d5a2233
Source dataset
uspto-grants-2005_08
Patent number
US06927226B2

Linked notes

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