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[ CAS No. 153037-40-2 ]

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Chemical Structure| 153037-40-2
Chemical Structure| 153037-40-2
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Product Details of [ 153037-40-2 ]

CAS No. :153037-40-2 MDL No. :MFCD28359224
Formula : C20H25NO3 Boiling Point : 514.5±50.0°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :327.42 g/mol Pubchem ID :54340554
Synonyms :

Safety of [ 153037-40-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 153037-40-2 ]

  • Upstream synthesis route of [ 153037-40-2 ]
  • Downstream synthetic route of [ 153037-40-2 ]

[ 153037-40-2 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 119273-61-9 ]
  • [ 153037-40-2 ]
YieldReaction ConditionsOperation in experiment
77%
Stage #1: With triethylamine In tetrahydrofuran at 0℃; for 0.25 h; Inert atmosphere
Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water at 0 - 20℃; Inert atmosphere
General procedure: (S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoic acid (2.65 g, 10 mmol) was dissolved in THF (20 ml) under a nitrogen atmosphere and cooled to 0 . Thriethylamine (1.42 ml, 1.1 eq) were then added to form a white precipitate. After 0.25 h, the solution was filtered. The filtrate was added to a solution of sodium borohydride (0.62 g, 1.5 eq) in water (8 ml) dropwise at 0 . After 0.5 h, the reaction mixture was warmed to room temperature and allowed to stir for a further 2 h. the reaction mixture was then acidified PH to 2 using 2 M hydrochloric acid and extracted with ethyl acetate. The organic layer was then washed with a saturated solution of NaHCO3, dried over MgSO4 and concentrated in vacuo to get compound 16a (1.88 g, 75percent).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 1208 - 1212
  • 2
  • [ 24424-99-5 ]
  • [ 153037-40-2 ]
  • [ 1426129-50-1 ]
YieldReaction ConditionsOperation in experiment
12.8 % ee With sodium carbonate In methanol; water at 20 - 80℃; for 5 h; 100 mL of a three-necked flask was added compound C-2 (1.9 g, 5 mmol, 1 eq), 10 mL of water, 30 mL of methanol,The temperature was raised to 70 to 80 ° C. The mixture was dissolved, sodium carbonate (1.6 g, 15 mmol, 3 eq) was added, and the mixture was slowly cooled to room temperature,BOC anhydride (1.1 g, 5 mmol, 1 eq) was added and stirred at room temperature for 5 h. The reaction solution was added with 100 mL of water,(30 mL * 2), the organic phases were combined, dried, concentrated, 5 mL of petroleum ether was added,The mixture was stirred for 15 minutes, filtered and the cake was dried to give Compound B (1.4 g, yield: 85percent, eepercent: 12.8percent)
Reference: [1] Patent: CN105017082, 2017, B, . Location in patent: Paragraph 0070-0072
  • 3
  • [ 24424-99-5 ]
  • [ 153037-40-2 ]
  • [ 1426129-50-1 ]
YieldReaction ConditionsOperation in experiment
20.6 % ee With potassium carbonate In ethanol; water at 20 - 80℃; for 1 h; 100 mL of a three-necked flask was added compound C-3 (3.3 g, 5.3 mmol, 1 eq), 10 mL of water was added,30 mL of ethanol, the temperature was raised to 70 to 80 ° C, the mixture was dissolved, potassium carbonate (2.2 g, 15 mmol, 3 eq)Slowly cool to room temperature, BOC anhydride (1.4 g, 6 mmol, 1.2 eq) was added and stirred at room temperature for 1 h.The reaction solution was added to 50 mL of water, extracted with DCM (30 mL * 2), combined with the organic phase, dried, concentrated,The mixture was stirred for 15 minutes, filtered and the cake was dried to give Compound B (1.5 g, yield: 85percent, eepercent: 20.6percent).
Reference: [1] Patent: CN105017082, 2017, B, . Location in patent: Paragraph 0076-0078
  • 4
  • [ 24424-99-5 ]
  • [ 153037-40-2 ]
  • [ 1426129-50-1 ]
YieldReaction ConditionsOperation in experiment
52.2 % ee With potassium hydroxide In tetrahydrofuran; water at 20℃; for 5 h; 100 mL of a three-necked flask was added compound C (1.4 g, 3.7 mmol, 1 eq), 10 mL of water, 30 mL of THF,The temperature was raised to 70 to 80 ° C, the mixture was dissolved, and a 4N NaOH aqueous solution (2.8 mL, 11 mmol, 3 eq)Slowly cool to room temperature, BOC anhydride (1 g, 4.5 mmol, 1.2 eq) was added and stirred at room temperature for 3 h.The reaction solution was added to 50 mL of water, extracted with DCM (30 mL * 2), combined with the organic phase, dried, concentrated,Add 5mL petroleum ether beating, stirring for 15 minutes, filter, filter cake drying,Compound B (1.1 g, yield: 92percent, purity: 98.4percent, eepercent: 99.2percent) was obtained.
Reference: [1] Patent: CN105017082, 2017, B, . Location in patent: Paragraph 0064-0066
  • 5
  • [ 109-02-4 ]
  • [ 119273-61-9 ]
  • [ 543-27-1 ]
  • [ 153037-40-2 ]
Reference: [1] Patent: US5250522, 1993, A,
[2] Patent: US5550119, 1996, A,
  • 6
  • [ 119273-61-9 ]
  • [ 543-27-1 ]
  • [ 153037-40-2 ]
Reference: [1] Patent: US5550119, 1996, A,
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