Hydrochloric Acid → HCID 3720342, compound

HRID 2104401Notes

Reaction equation

HRID 2104401 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH:4]([NH2:13])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.[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>[CH3:1][O:2][C:3](=[O:14])[CH:4]([NH:13][S:21]([C:18]1[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=1)(=[O:23])=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=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

2-Amino-3-(4-fluorophenyl)propionic acid methyl ester (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 thereto, followed by heating under reflux for 4.5 hours. Additional p-toluenesulfonyl chloride (2.20 g) was added thereto, and the thus-obtained mixture was heated under reflux for 3.5 hours. The reaction mixture was poured into ice and 1N HCl (17 mL) to partition the mixture. The organic layer was sequentially washed with saturated aqueous sodium hydrogencarbonate and saturated brine, and was dried over sodium sulfate anhydrate. The solvent was distilled away under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1->2:1), to thereby give the title compound (2.89 g).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 4.5 hours
  3. temperaturethe thus-obtained mixture was heated
  4. temperatureunder reflux for 3.5 hours
  5. customto partition the mixture
  6. washThe organic layer was sequentially washed with saturated aqueous sodium hydrogencarbonate and saturated brine
  7. dry with materialwas dried over sodium sulfate anhydrate
  8. distillationThe solvent was distilled away under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1->2:1)

Sources & evidence

ORD record
ord-78d6d5395fbc45aeb7bd27c8e4b24e3d
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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