Potassium Carbonate → HCID 57827708, compound

HRID 1842159Notes

Reaction equation

HRID 1842159 reaction equation
C([N:9]=[C:10]=[S:11])(=O)C1C=CC=CC=1.[NH2:12][C@@:13]1([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Br:26])[CH:21]=2)[CH2:18][CH2:17][O:16][CH2:15][C@@H:14]1[OH:19].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O1CCCC1.CO>[Br:26][C:22]1[CH:21]=[C:20]([C@:13]2([NH:12][C:10]([NH2:9])=[S:11])[CH2:18][CH2:17][O:16][CH2:15][C@@H:14]2[OH:19])[CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 68284Benzoyl isothiocyanateHCID 57827141HCID 57827141, compound

Product 1

HCID 57827708HCID 57827708, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Benzoyl isothiocyanate (7.20 g) was added to a suspension of (±)-(3R*,4R*)-4-amino-4-(3-bromophenyl)tetrahydropyran-3-ol (10.9 g) in toluene (200 mL). The mixture was stirred at room temperature overnight and then diluted with tetrahydrofuran, followed by addition of silica gel. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to obtain an intermediate crude product. The resulting intermediate was suspended in methanol (300 mL), and potassium carbonate (20.0 g) was added. The mixture was stirred at room temperature overnight. Then, the insoluble matter was removed by filtration through celite, and the solvent was evaporated under reduced pressure. The residue was diluted with ethyl acetate, and the resulting solid was removed by filtration through celite. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound (8.63 g).

Workup

  1. additionfollowed by addition of silica gel
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography
  4. customto obtain an intermediate crude product
  5. stirringThe mixture was stirred at room temperature overnight
  6. customThen, the insoluble matter was removed by filtration through celite
  7. customthe solvent was evaporated under reduced pressure
  8. additionThe residue was diluted with ethyl acetate
  9. customthe resulting solid was removed by filtration through celite
  10. customThe solvent was evaporated under reduced pressure
  11. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-49bd6d7055f749a59d0c08baf4259332
Source dataset
uspto-grants-2015_02
Patent number
US08946211B2

Reaction notes

Loading…