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Chemical Structure| 773038-42-9 Chemical Structure| 773038-42-9

Structure of 773038-42-9

Chemical Structure| 773038-42-9

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Product Details of [ 773038-42-9 ]

CAS No. :773038-42-9
Formula : C8H15NO3
M.W : 173.21
SMILES Code : O=C(O)[C@@H](N)C1CCC(O)CC1
MDL No. :MFCD18252693

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Application In Synthesis of [ 773038-42-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 773038-42-9 ]

[ 773038-42-9 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 32462-30-9 ]
  • [ 773038-42-9 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; hydrogen;nickel; In water; at 80℃; under 5148.66 Torr; for 3h; (1) 4-Hydroxy-L-phenylglycine (21.56 g) was dissolved in water (250 mL) and 3 mol/L aqueous sodium hydroxide solution (43 mL). Raney-nickel (130 g) was added to conduct hydrogenation reaction under heating at 80°C and 7.0 kgf/cm2. After 3 hr, the reaction mixture was filtered, and the solid was washed with water. The filtrate was concentrated under reduced pressure to 200 mL. 1,4-Dioxane (150 mL) and triethylamine (32 mL) were added to the concentrated solution, di-tert-butyl dicarbonate (33.8 g) was added under ice-cooling, and the mixture was stirred at room temperature for 20 hr. The organic solvent was evaporated from the reaction mixture, and 2 mol/L hydrochloric acid (155 mL) was poured thereinto under ice-cooling to adjust the mixture to pH 2. Sodium chloride was added to saturation and the mixture was extracted 4 times with ethyl acetate. The extract was dried and concentrated under reduced pressure. THF (350 mL) and 1,3-thiazolidine (13.8 g) were added to the residue, HOBT (30.40 g) and EDC hydrochloride (29.7 g) were successively added under ice-cooling, and the mixture was stirred at room temperature for 12 hr. The reaction mixture was concentrated, and saturated aqueous sodium hydrogencarbonate solution was added to the concentrate. The mixture was extracted with chloroform and the extract was dried. The solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography to give 3-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-1-cyclohexyl)acetyl]-1,3-thiazolidine (41.66 g, yield 93.8percent) as a white solid.
 

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