Water → HCID 59846309, compound

HRID 1363232Notes

Reaction equation

HRID 1363232 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([NH:5][C@H:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([F:16])[CH:14]=2)[CH2:9][CH2:8][CH2:7]1)=[O:4].O.O.O.O.O.O.O.S([O-])([O-])(=O)=[O:27].[Mg+2].O.[K]>CC(C)=O>[F:18][C:2]([F:1])([F:17])[C:3]([NH:5][C@H:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([F:16])[CH:14]=2)[C:9](=[O:27])[CH2:8][CH2:7]1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 24843Magnesium Sulfate HeptahydrateHCID 5462222PotassiumHCID 59846479HCID 59846479, compound

Product 1

HCID 59846309HCID 59846309, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of (R)-2,2,2-trifluoro-N-(7-fluoro-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide (3.51 g, 13.4 mmol, 1 equiv) in acetone (217 mL) was added magnesium sulfate heptahydrate (9.92 g, 40.3 mmol, 3 equiv) with water (167 mL). The mixture was stirred in ice bath. Potassium permangnate (6.37 g, 40.3 mmol, 3 equiv) was added in portions within 1 hour period. After addition, the reaction mixture was stirred at RT for 16 h. The resulting black solid was filtered off and washed with acetone. The combined filtrate and washings were diluted with CH2Cl2 (200 mL). The aqueous phase was separated and washed with CH2Cl2. The CH2Cl2 solution was washed with saturated Na2S2O7 solution (150 mL). The resulting black solid was filtered off The filtrate was evaporated to remove organic solvents. The concentrate was diluted with CH2Cl2 (400 mL). The aqueous phase was separated and washed with CH2Cl2. The combined CH2Cl2 phase was concentrated to give a white solid product (3.54 g, 96%). 1H NMR (400 MHz, DMSO-d6) δ 10.00 (s, 1H), 8.00 (q, 1H), 7.30-7.36 (m, 1H), 7.15 (dd, 1H), 5.32-5.38 (m, 1H), 2.60-2.85 (m, 2H), 2.16-2.30 (m, 2H).

Workup

  1. additionAfter addition
  2. stirringthe reaction mixture was stirred at RT for 16 h
  3. filtrationThe resulting black solid was filtered off
  4. washwashed with acetone
  5. additionThe combined filtrate and washings were diluted with CH2Cl2 (200 mL)
  6. customThe aqueous phase was separated
  7. washwashed with CH2Cl2
  8. washThe CH2Cl2 solution was washed with saturated Na2S2O7 solution (150 mL)
  9. filtrationThe resulting black solid was filtered off The filtrate
  10. customwas evaporated
  11. customto remove organic solvents
  12. additionThe concentrate was diluted with CH2Cl2 (400 mL)
  13. customThe aqueous phase was separated
  14. washwashed with CH2Cl2
  15. concentrationThe combined CH2Cl2 phase was concentrated

Sources & evidence

ORD record
ord-85dd8ae8f6e64fdcaedc737a00b19082
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

Loading…