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Chemical Structure| 35455-21-1 Chemical Structure| 35455-21-1

Structure of 35455-21-1

Chemical Structure| 35455-21-1

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Product Details of [ 35455-21-1 ]

CAS No. :35455-21-1
Formula : C3H6FNO2
M.W : 107.08
SMILES Code : N[C@@H](CF)C(O)=O
English Name :(R)-2-Amino-3-fluoropropanoic acid
MDL No. :MFCD19203448

Safety of [ 35455-21-1 ]

Application In Synthesis of [ 35455-21-1 ]

* 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 [ 35455-21-1 ]

[ 35455-21-1 ] Synthesis Path-Downstream   1~3

  • 1
  • [ CAS Unavailable ]
  • [ 35455-21-1 ]
  • [ 58632-95-4 ]
  • [ 76399-81-0 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In acetone - water 58 N-(1-Carboxy-3-phenylpropyl)-L-3-fluoroalanyl-L-proline EXAMPLE 58 N-(1-Carboxy-3-phenylpropyl)-L-3-fluoroalanyl-L-proline To a solution of L-3-fluoroalanine (420 mg) in 4 ml acetone-water (1:1) is added triethylamine (590 mg) and 2-t-butoxycarbonyloximino-2-phenylacetonitrile (1.060 g). The mixture is stirred 2.5 hr. Cold 5% aqueous potassium bicarbonate solution is added and the mixture is extracted with ethyl acetate. The aqueous phase is acidified with cold 1 N hydrochloric acid and extracted with ethyl acetate. The latter extract is washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated to dryness to give L-t-BOC-3-fluoroalanine (800 mg), m.p. 91°-93°.
  • 2
  • [ 35455-21-1 ]
  • [ 501-53-1 ]
  • [ 36369-34-3 ]
YieldReaction ConditionsOperation in experiment
In sodium hydroxide; Petroleum ether; (i) A solution of 0.535 g (5 mmol) of D,L-3-fluoroalanine in 1.25 ml (5 mmol) of 4 N sodium hydroxide was stirred at 5 C. while 0.935 g (5.5 mmol) of benzyl chloroformate and 1.5 ml (6 mmol) of 4 N sodium hydroxide were added alternately in five portions of each and while maintaining the temperature at below 10 C. and the pH at greater than 11. The mixture was stirred for a further 1 hour at 0 C. as the temperature was allowed to rise to room temperature. The mixture was stirred overnight at room temperature. 2 ml of ether were then added and the resulting mixture was stirred vigorously at room temperature for 1 hour. The organic and aqueous layers were separated and the aqueous layer was extracted with 5 ml of ether. The aqueous layer was cooled to 10 C. and treated dropwise with 1.2 ml of 5 N hydrochloric acid until the mixture became acid to Congo Red. The mixture was then stirred for a further 2 hours at 10 C. when a solid crystallized from the solution. This solid was filtered off and washed with a minimum volume of ice-cold water. The solid was dissolved in 10 ml of ether and the solution washed with two 10 ml portions of cold (0 C.) water. The ether solution was dried over sodium sulphate and evaporated to yield a solid which was triturated with petroleum ether. The solid was filtered off and dried to give 0.6 g of product of melting point 108-110 C. (decomposition). Recrystallisation of 0.1 g of this product from a mixture of 0.5 ml of ether and 0.5 ml of petroleum ether gave ca.60 mg of N-benzyloxycarbonyl-D,L-3-fluoroalanine of melting point 112-114 C. (decomposition).
(i) In a manner analogous to that described in Example 1, from 2.9 g (27 mmol) of L-3-fluoroalanine and 5.1 g (30 mmol) of benzyl chloroformate there were obtained 4.4 g of N-benzyloxycarbonyl-L-3-fluoroalanine of melting point 110-116 C. (decomposition; softening at 140 C.), [alpha]D20 = +5.4 (c = 0.5% in glacial acetic acid). Recrystallisation from a mixture of 25 ml of ether and 25 ml of petroleum ether gave 3.7 g of N-benzyloxycarbonyl-L-3-fluoroalanine of melting point 108-115 C. (decomposition; softening at 104 C.); [alpha]D20 = +5.6 (c = 0.5% in glacial acetic acid).
  • 3
  • [ 35455-21-1 ]
  • [ 24424-99-5 ]
  • [ 76399-81-0 ]
YieldReaction ConditionsOperation in experiment
93% Stage #1: (R)-3-fluoroalanine; di-<i>tert</i>-butyl dicarbonate With sodium carbonate In tetrahydrofuran; water at 20℃; Stage #2: With citric acid In water 11 A mixture of unprotected amino acid a (775 mg, 7.24 mmol) and sodium carbonate (1.69 g, 16.0 mmol) was dissolved in a 1 : 1 solution of deionized water and THF (15 mL each). To this mixture was added BOC-anhydride b (1.73 g, 7.96 mmol). The mixture was stirred at room temperature overnight, and THF was removed under reduced pressure. The mixture was then acidified to pH 2-3 with saturated aqueous citric acid, and product was extracted into 10% ethyl acetate- dichloromethane. The organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure to afford clean BOC-protected amino acid c (1.40 g, 6.7 mmol, 93%) to be used without further purification.
 

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