Hydrochloric Acid → HCID 15463533, compound

HRID 1108116Notes

Reaction equation

HRID 1108116 reaction equation
[C:1]([NH:8][C@@H:9]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:10](=[O:17])[C:11]([O:13][CH:14]([CH3:16])[CH3:15])=[O:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].Cl>C(O)(C)C>[C:1]([NH:8][C@@H:9]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C@H:10]([OH:17])[C:11]([O:13][CH:14]([CH3:16])[CH3:15])=[O:12])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11143Aluminum isopropoxideHCID 15463532HCID 15463532, compound

Product 1

HCID 15463533HCID 15463533, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In 10 ml of isopropanol was dissolved 1.0 g of isopropyl (3S)-3-(N-Boc)amino-4-phenyl-2-oxobutyrate, followed by addition of 0.7 g of aluminium isopropoxide, and heating under reflux for 4 hours. After the termination of the reaction was confirmed, an aqueous 1N hydrochloric acid solution was added to the resulting mixture, to adjust the mixture to pH 3.0, and the resulting mixture was concentrated under reduced pressure. The concentrate was diluted with ethyl acetate and water, followed by layer separation, and the resulting aqueous layer was extracted in ethyl acetate. The extract solution was washed in water and saturated sodium chloride solution, and dried over anhydrous magnesium sulfate, followed by filtration and concentration, to obtain 0.95 g of isopropyl (2S, 3S)-3-(N-Boc)amino-4-phenyl-2-hydroxybutyrate in a yield of 94.5%. The results of the HPLC analysis thereof are shown below. HPLC analysis conditions

Workup

  1. temperatureheating
  2. temperatureunder reflux for 4 hours
  3. concentrationthe resulting mixture was concentrated under reduced pressure
  4. additionThe concentrate was diluted with ethyl acetate and water
  5. customfollowed by layer separation
  6. extractionthe resulting aqueous layer was extracted in ethyl acetate
  7. washThe extract solution was washed in water
  8. dry with materialsaturated sodium chloride solution, and dried over anhydrous magnesium sulfate
  9. filtrationfollowed by filtration and concentration

Sources & evidence

ORD record
ord-2431a114408148e7a31cd0d3f9706ac6
Source dataset
uspto-grants-2000_05
Patent number
US06063955

Reaction notes

Loading…