Thionyl Chloride → HCID 86698259, compound

HRID 879245Notes

Reaction equation

HRID 879245 reaction equation
F[C:2](F)(F)C([O-])=O.[Na+].[NH2:9][C@@H:10]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:11][O:12][CH2:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.S(Cl)([Cl:43])=O>CO>[ClH:43].[CH3:2][O:19][C:18](=[O:20])[C:17]1[CH:21]=[CH:22][C:14]([CH2:13][O:12][CH2:11][C@@H:10]([NH2:9])[CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 85570p-ToluenesulfonateHCID 89824209HCID 89824209, compound

Product 1

HCID 86698259HCID 86698259, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

51.2 mg (128 μmol) of 4-({[(2S)-2-amino-3-phenylpropyl]oxy}methyl)benzoic acid sodium trifluoracetate were added to 5 ml of methanol and mixed with 2.4 mg (13 μmol) of 4-toluenesulfonate acid monohydrate. The batch was stirred overnight under reflux. Then, 18.7 μl (256 μmol) of thionyl chloride were added and the composition heated again under reflux for 6 hours. Then the reaction composition was evaporated in the rotating steam boiler and the residue vacuum dried. Thus, 42.3 mg (80% purity, 88% o. th.) of the title compound were obtained which were used in the consecutive reaction without further purification.

Workup

  1. temperatureunder reflux
  2. temperaturethe composition heated again
  3. temperatureunder reflux for 6 hours
  4. customThen the reaction composition was evaporated in the rotating steam boiler
  5. customthe residue vacuum dried

Sources & evidence

ORD record
ord-70df11438fe441eb9e548813e4af2120
Source dataset
uspto-grants-2015_03
Patent number
US08987209B2

Reaction notes

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