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[ CAS No. 114873-01-7 ]

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Chemical Structure| 114873-01-7
Chemical Structure| 114873-01-7
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Product Details of [ 114873-01-7 ]

CAS No. :114873-01-7 MDL No. :MFCD00672522
Formula : C14H18FNO4 Boiling Point : 425°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :283.30 g/mol Pubchem ID :2734492
Synonyms :

Safety of [ 114873-01-7 ]

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 [ 114873-01-7 ]

  • Upstream synthesis route of [ 114873-01-7 ]
  • Downstream synthetic route of [ 114873-01-7 ]

[ 114873-01-7 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 24424-99-5 ]
  • [ 19883-77-3 ]
  • [ 114873-01-7 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With sodium carbonate In 1,4-dioxane; water at 0 - 20℃; for 5 h;
Stage #2: With citric acid In water
A mixture of L-2-AMINO-3- (3-FLUORO- phenyl)-propionic acid (20.0 g, 110 MMOL, 1 eq) in H20 (100 mL) was treated with NA2CO3 (16.2 g, 153 mmol, 1.4 eq) in H20 (40 mL) followed by 1,4-dioxane (100 mL) and cooled to 0 C. The BOZO was added and the reaction mixture was stirred at ambient temperature for 5 h after which the- dioxane was evaporated. H2O (125 mL) was then added and the mixture then washed with Et2O (2 x 100 mL). The aqueous phase was acidified with 10percent citric acid followed by extraction with EtOAc (2 x 300 mL). The combined EtOAc layers were washed with H20 (2 x 150 mL), brine (150 mL), dried (Na2SO4) and concentrated to give the acid as a colorless, viscous oil which slowly solidified upon standing (31 G, QUANT). H NMR (CDC13) 7.33-7. 26 (m, 1H), 7.00-6. 91 (m, 3H), 4.96 (s, 1H), 4.62 (bs, 1H), 3.23 (dd, J=14, 5.3, 2H), 1. 44 (s, 9H) ; Anal CALCD for C14HL8NO4F : C, 59.36 ; H, 6.40 ; N, 4.94. Found: C, 59.29 ; H, 6.34 ; N, 4.90.
100% With sodium carbonate In 1,4-dioxane; water at 0 - 25℃; for 5 h; A mixture of BOC-L-3-fluorophenylalanine 1 (20 g, 109 MMOL) in water was treated with sodium carbonate (16.2 g, 15.3 MMOL) in H20 (40 mL). 1,4-Dioxane (100 mL) was added, and the mixture cooled to 0 °C. The BOC20 (28. 6 g, 120 MMOL) was added in one portion, and the mixture was maintained for 5 h at 25 °C. The solvent was evaporated and H2O (125 mL) was added. The aqueous layer was washed with diethyl ether (2 x 100 mL). The ether layers were discarded, and the aqueous layer was acidified with a 10percent citric acid solution. The mixture was then extracted with EtOAc (2 x 150 mL). The organic layers were combined, washed with H20 (2 x 150 mL), Brine (150 mL), dried (NA2SO4), filtered and evaporated to give the desire crude product 2 as a clear viscous oil. 30.9 9, 100percent, ) which slowly solidified to a white solid at rt. 1H NMR (300 MHz, CDCl3) 8 7.33-7. 26 (M, 1H), 7.00-6. 91 (m, 3H), 4.96 (s, 1H), 4.62 (bs, 1H), 3.23 (dd, J= 14,5. 3 Hz, 2H), 1.44 (s, 9H) ppm; Anal CALCD for CR4HR8NO4F : C, 59.36 ; H, 6.40 ; N, 4.94. Found: C, 59.29 ; H, 6.34 ; N, 4.90.
Reference: [1] Patent: WO2005/26114, 2005, A1, . Location in patent: Page/Page column 85
[2] Patent: WO2005/26114, 2005, A1, . Location in patent: Page/Page column 102
[3] Journal of Medicinal Chemistry, 1994, vol. 37, # 13, p. 2090 - 2099
  • 2
  • [ 19883-77-3 ]
  • [ 114873-01-7 ]
YieldReaction ConditionsOperation in experiment
85% With sodium carbonate In water; acetonitrile at 25℃; for 12 h; General procedure: L-Phenylalanine (1.0 g, 6.05 mmol) and sodium carbonate (0.71 g, 6.70 mmol) in water (10 mL) was reacted with a solution of 2 (1.89 g, 6.36 mmol) in acetone (10 mL). The reaction mixture was stirred at room temperature till the reaction completes, as monitored by TLC. The resulting solution was concentrated, to the residue was added water (10 mL) and ethyl acetate (10 mL), pH adjusted to 6.0 with 10percent KHSO4 and stirred for 5 minutes. The organic layer was removed and the aqueous layer was acidified to pH 2.0 with 10percent KHSO4 at 0-5°C and extracted with ethyl acetate (2 x 10 mL). The combined organic layers were washed with 5percent NaHCO3 solution, water, brine and dried over anhydrous Na2SO4. The ethyl acetate layer was concentrated and the residue was crystallized from EtOAc/ n-hexane (2:8) mixture to give the product as a white solid (1.53g, 95percent yield).
Reference: [1] Synthetic Communications, 2017, vol. 47, # 22, p. 2127 - 2132
  • 3
  • [ 24424-99-5 ]
  • [ 114873-01-7 ]
Reference: [1] Synthetic Communications, 2017, vol. 47, # 22, p. 2127 - 2132
  • 4
  • [ 58632-95-4 ]
  • [ 19883-77-3 ]
  • [ 114873-01-7 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1989, vol. 37, # 3, p. 826 - 828
  • 5
  • [ 114873-01-7 ]
  • [ 1047644-62-1 ]
Reference: [1] Drugs of the Future, 2014, vol. 39, # 8, p. 541 - 546
  • 6
  • [ 114873-01-7 ]
  • [ 1201923-48-9 ]
Reference: [1] Drugs of the Future, 2014, vol. 39, # 8, p. 541 - 546
[2] Patent: US2013/96144, 2013, A1,
[3] Patent: WO2009/158371, 2009, A1,
[4] Patent: WO2009/158372, 2009, A1,
[5] Patent: WO2009/158374, 2009, A2,
  • 7
  • [ 114873-01-7 ]
  • [ 1202237-87-3 ]
Reference: [1] Patent: US2013/96144, 2013, A1,
[2] Patent: WO2009/158371, 2009, A1,
[3] Patent: WO2009/158372, 2009, A1,
[4] Patent: WO2009/158374, 2009, A2,
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