HCID 12082209, compound → HCID 22663115, compound

HRID 392127Notes

Reaction equation

HRID 392127 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][C@@H:13]2[O:18][C:17]3[C:19]([CH:26]=O)=[C:20]([N+:23]([O-:25])=O)[CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.O.O.O.C([O-])(=O)C.[Na+]>O1CCCC1.CO>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][CH2:12][CH:13]2[O:18][C:17]3[C:19]4=[CH:26][O:25][N:23]=[C:20]4[CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 12082209HCID 12082209, compoundHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 22663115HCID 22663115, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

19.7 g (87.4 mmole) of stannous chloride dihydrate was added to a solution of 6.62 g (17.5 mmole) of (2R)-(8-formyl-7-nitro-2,3-dihydro-1,4-benzodioxin-2-yl)methyl 4-methylbenzenesulfonate in 400 mL of 1:1 tetrahydrofuran/methanol followed by the addition of 23.8 g (0.17 mole) of sodium acetate trihydrate. The mixture was stirred under nitrogen for a period of 48 hours. The solvent was removed in vacuo and replaced with an equal amount of methylene chloride and the solution was washed with 400 mL portions of saturated aqueous sodium bicarbonate and saturated brine and dried over magnesium sulfate. After the solution was filtered and concentrated in vacuum, the crude oil obtained was column chromatographed on silica gel with methylene chloride as eluant and the product fractions were combined and evaporated in vacuum to give 4.47 g (71%) of the (R)-enantiomer of the title compound as a light yellow solid, m.p.109-110° C.

Workup

  1. customThe solvent was removed in vacuo
  2. washthe solution was washed with 400 mL portions of saturated aqueous sodium bicarbonate and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationAfter the solution was filtered
  5. concentrationconcentrated in vacuum
  6. customthe crude oil obtained
  7. customchromatographed on silica gel with methylene chloride as eluant
  8. customevaporated in vacuum

Sources & evidence

ORD record
ord-c6692cc01a6e45448fff0c9ba603720a
Source dataset
uspto-grants-2004_10
Patent number
US06800642B2

Reaction notes

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