Hydrochloric Acid → HCID 3720342, compound

HRID 902874Notes

Reaction equation

HRID 902874 reaction equation
[NH2:1][CH:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.N1C=CC=CC=1.Cl>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[F:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][CH:2]([NH:1][S:21]([C:18]2[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=2)(=[O:23])=[O:22])[C:3]([O:5][CH3:6])=[O:4])=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chloride2×HCID 437626methyl 2-amino-3-(4-fluorophenyl)propanoate

Product 1

HCID 3720342HCID 3720342, compoundYield 80.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

Methyl 2-amino-3-(4-fluorophenyl)propionate (2.01 g), p-toluenesulfonyl chloride (2.25 g) and 4-dimethylaminopyridine (309 mg) were dissolved in chloroform (30 ml), and pyridine (3.0 ml) was added to heat the mixture under reflux for 4.5 hours. P-Toluenesulfonyl chloride (2.20 g) was additionally added, and the mixture was heated under reflux for 3.5 hours. The reaction mixture was poured into ice and 1N hydrochloric acid (17 ml) to conduct liquid separation. The resultant organic layer was successively washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate 9:1→2:1) to obtain the title compound (2.89 g).

Workup

  1. temperatureto heat the mixture
  2. temperatureunder reflux for 4.5 hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 3.5 hours
  5. customliquid separation
  6. washThe resultant organic layer was successively washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate 9:1→2:1)

Sources & evidence

ORD record
ord-243e911d99f84248979d325f46295ac4
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Reaction notes

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