Sodium Sulfite → HCID 86657026, compound

HRID 1909111Notes

Reaction equation

HRID 1909111 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[N:6][CH:7]=1.ClC1C=CC=C(C(OO)=[O:26])C=1.S([O-])([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[N+:6]([O-:26])[CH:7]=1

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-9af8c24634fb4cbfadbc22bb6edd6009
Source dataset
uspto-grants-2013_12
Patent number
US08598209B2

Reaction notes

Loading…