Hydrochloric Acid → HCID 59281217, compound

HRID 217996Notes

Reaction equation

HRID 217996 reaction equation
[NH2:1][C@@:2]1([C:19]2[CH:24]=[C:23]([Br:25])[CH:22]=[CH:21][C:20]=2[F:26])[CH2:7][O:6][C@@H:5]([CH2:8][O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:4][C@H:3]1[CH2:17]O.C([N:35]=[C:36]=[S:37])(=O)C1C=CC=CC=1.Cl>ClCCl.CO>[CH2:10]([O:9][CH2:8][C@@H:5]1[O:6][CH2:7][C@@:2]2([C:19]3[CH:24]=[C:23]([Br:25])[CH:22]=[CH:21][C:20]=3[F:26])[C@H:3]([CH2:17][S:37][C:36]([NH2:35])=[N:1]2)[CH2:4]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 68284Benzoyl isothiocyanateHCID 59281210[(2R,4R,5S)-5-amino-2-benzyloxymethyl-5-(5-bromo-2-fluorophenyl)tetrahydropyran-4-yl]methanol

Product 1

HCID 59281217HCID 59281217, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

[(2R,4R,5S)-5-Amino-2-benzyloxymethyl-5-(5-bromo-2-fluorophenyl)tetrahydropyran-4-yl]methanol (2.22 g) was dissolved in dichloromethane (30 ml), and benzoyl isothiocyanate (776 μl) was added. The mixture was stirred at room temperature for five hours, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain an intermediate. The resulting intermediate was dissolved in methanol (50 ml), and concentrated hydrochloric acid (2 ml) was added. The mixture was heated under reflux for six hours and then cooled to room temperature. The solvent was evaporated under reduced pressure. Methanol (30 ml) and DBU (2 ml) were added to the residue, followed by heating under reflux for three hours. The reaction solution was cooled to room temperature, and the solvent was evaporated under reduced pressure. The residue was purified by NH-silica gel column chromatography to obtain the title compound (2.30 g).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography
  3. customto obtain an intermediate
  4. temperatureThe mixture was heated
  5. temperatureunder reflux for six hours
  6. temperaturecooled to room temperature
  7. customThe solvent was evaporated under reduced pressure
  8. additionMethanol (30 ml) and DBU (2 ml) were added to the residue
  9. temperatureby heating
  10. temperatureunder reflux for three hours
  11. temperatureThe reaction solution was cooled to room temperature
  12. customthe solvent was evaporated under reduced pressure
  13. customThe residue was purified by NH-silica gel column chromatography

Sources & evidence

ORD record
ord-f4597f2fcba24b7cb90bf2551bec114e
Source dataset
uspto-grants-2012_06
Patent number
US08198269B2

Reaction notes

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