Sodium Sulfite → HCID 86657026, compound

HRID 888349Notes

Reaction equation

HRID 888349 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C@@H:8]([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][N:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:26])C=1.S([O-])([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[C:1]([O:5][C:6](=[O:17])[NH:7][C@@H:8]([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][N+:11]=1[O-:26])[CH3:9])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acid2×HCID 516892Sodium BicarbonateHCID 70650627HCID 70650627, compound

Product 1

HCID 86657026HCID 86657026, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl[(1R)-1-(5-fluoropyridin-2-yl)ethyl]carbamate (5.77 g, 24.0 mmol) in dichloromethane (96 mL) was added 3-chloroperbenzoic acid (6.51 g, 26.4 mmol). After 4.5 h, excess 3-chloroperbenzoic acid (0.59 g, 2.6 mmol) was added. After 72 h, saturated aqueous sodium sulfite was added. After 1 h, saturated aqueous sodium bicarbonate was added. The organic layer was isolated and the aqueous layer was extracted with dichloromethane (2×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated. Purification by silica gel chromatography (100% dichloromethane→90% dichloromethane/methanol with 1% ammonium hydroxide) gave the title compound (5.45 g). MS 257.1 (M+1).

Workup

  1. waitAfter 72 h
  2. waitAfter 1 h
  3. customThe organic layer was isolated
  4. extractionthe aqueous layer was extracted with dichloromethane (2×)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by silica gel chromatography (100% dichloromethane→90% dichloromethane/methanol with 1% ammonium hydroxide)

Sources & evidence

ORD record
ord-506a8973b6674193b77f92001d6511c2
Source dataset
uspto-grants-2012_08
Patent number
US08247401B2

Reaction notes

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