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114457-94-2

Basic Information
CAS No.: 114457-94-2
Name: (S)-3-PHENYL-2-[(PYRAZIN-2-YLCARBONYL)AMINO] PROPANOIC ACID
Article Data: 26
Molecular Structure:
Molecular Structure of 114457-94-2 ((S)-3-PHENYL-2-[(PYRAZIN-2-YLCARBONYL)AMINO] PROPANOIC ACID)
Formula: C14H13N3O3
Molecular Weight: 271.276
Synonyms: (S)-3-Phenyl-2-[(pyrazin-2-ylcarbonyl)amino] propanoic acid;
Density: 1.323 g/cm3
Melting Point: 166-169℃
Boiling Point: 573.8 °C at 760 mmHg
Flash Point: 300.8 °C
PSA: 92.18000
LogP: 1.29320
Synthetic route

(pyrazine-2-carbonyl)-L-phenylalanine ethyl ester

114457-94-2

(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

Conditions
ConditionsYield
With sodium hydroxide In water; acetone at 0℃; for 2h;99%
63-91-2

L-phenylalanine

306990-94-3

(1H-benzo[d][1,2,3]triazol-1-yl)(pyrazin-2-yl)methanone

114457-94-2

(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

Conditions
ConditionsYield
With trialkylamine In water; acetonitrile at 20℃;98%
7364-51-4

N,O-bis(trimethylsilyl)phenylalanine

103435-88-7

pyrazinecarboxylic acid imidazolide

114457-94-2

(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

Conditions
ConditionsYield
Stage #1: N,O-bis(trimethylsilyl)phenylalanine; pyrazinecarboxylic acid imidazolide In dichloromethane at -40 - 20℃; for 19.5h;
Stage #2: With water; citric acid In dichloromethane
97%
In dichloromethane at -40 - 20℃; for 16.5h;0.96 g

C18H21N3O3

114457-94-2

(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃; for 2h;96%
73058-37-4

N-(2-pyrazinylcarbonyl)-L-phenylalanine methyl ester

114457-94-2

(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

Conditions
ConditionsYield
With sodium hydroxide In acetone pH=12 - Ca. 13; Cooling with ice;93.6%
With lithium hydroxide In tetrahydrofuran; water at 0℃; for 1h;93%
With sodium hydroxide In 1,4-dioxane; methanol for 1h;69%

Phe-Wang resin

18414-58-9

diphenylmethylsilanecarboxylic acid

32111-21-0

2-iodopyrazine

114457-94-2

(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

Conditions
ConditionsYield
Stage #1: Phe-Wang resin; diphenylmethylsilanecarboxylic acid; 2-iodopyrazine With potassium fluoride; C39H32OP2*C13H12N(1-)*Pd(2+)*CH3O3S(1-); triethylamine In N,N-dimethyl-formamide at 20℃; for 15h; wang polystyrene resin; Sealed tube; Inert atmosphere;
Stage #2: With triethylsilane; trifluoroacetic acid In water at 20℃; for 2h; Sealed tube; Inert atmosphere;
82%
19847-10-0

pyrazinoyl chloride

63-91-2

L-phenylalanine

114457-94-2

(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

Conditions
ConditionsYield
Stage #1: pyrazinoyl chloride; L-phenylalanine With sodium carbonate In water; toluene at 10 - 25℃; for 3h;
Stage #2: With hydrogenchloride In methanol; water at 15 - 20℃; pH=3;
36%
With sodium carbonate In water; toluene at 10 - 25℃;36%

A

Pyrazine-2-carboxylic acid ((S)-1-carbamoyl-2-phenyl-ethyl)-amide

B

114457-94-2

(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

Conditions
ConditionsYield
With sodium hydroxide; oxygen In dimethyl sulfoxide at 70℃; for 250h; pH=12.0; Kinetics; Product distribution; Oxidation; hydrolysis;
With sodium hydroxide; oxygen at 70℃; for 48h; pH=12; Oxidation; hydrolysis;

A

Pyrazine-2-carboxylic acid ((S)-1-carbamoyl-2-phenyl-ethyl)-amide

B

114457-94-2

(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

C

289472-78-2

Pyrazine-2-carboxylic acid [(S)-1-((R)-1-hydroxy-3-methyl-butylcarbamoyl)-2-phenyl-ethyl]-amide

D

Pyrazine-2-carboxylic acid [(S)-1-((S)-1-hydroxy-3-methyl-butylcarbamoyl)-2-phenyl-ethyl]-amide

Conditions
ConditionsYield
With dihydrogen peroxide In water at 20℃; for 1h; Kinetics; Product distribution; Further Variations:; Solvents; Oxidation; hydrolysis;
114457-94-2

(S)-3-phenyl-2-[(pyrazine-2-carbonyl)amino]propanoic acid

Conditions
ConditionsYield
With hydrogenchloride; oxygen In dimethyl sulfoxide at 70℃; for 250h; pH=1.0; Kinetics; Product distribution; Oxidation; hydrolysis;
With hydrogenchloride; oxygen at 70℃; for 120h; pH=1.0; Oxidation; hydrolysis;
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  • (S)-3-PHENYL-2-[(PYRAZIN-2-YLCARBONYL)AMINO] PROPANOIC ACID

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  • N-(2-Pyrazinylcarbonyl)-L-phenylalanine

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    114457-94-2

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  • N-(2-pyrazinylcarbonyl)-l-phenylalanine

  • Casno:

    114457-94-2

    N-(2-pyrazinylcarbonyl)-l-phenylalanine

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Specification

The L-Phenylalanine,N-(2-pyrazinylcarbonyl)-, with the CAS registry number of 114457-94-2, is also known as (S)-3-Phenyl-2-[(pyrazin-2-ylcarbonyl)amino] propanoic acid. Its molecular formula is C14H13N3O3 and molecular weight is 271.27132. What's more, its systematic name is (2S)-3-Phenyl-2-(pyrazine-2-carbonylamino)propanoic acid.

Physical properties about the L-Phenylalanine,N-(2-pyrazinylcarbonyl)- are: (1)ACD/LogP: 0.48; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 6; (4)#H bond donors: 2; (5)#Freely Rotating Bonds: 5; (6)Polar Surface Area: 92.18 Å2; (7)Index of Refraction: 1.612; (8)Molar Refractivity: 71.33 cm3; (9)Molar Volume: 204.9 cm3; (10)Surface Tension: 63.9 dyne/cm; (11)Density: 1.323 g/cm3; (12)Flash Point: 300.8 °C; (13)Enthalpy of Vaporization: 90.45 kJ/mol; (14)Boiling Point: 573.8 °C at 760 mmHg; (15)Vapour Pressure: 5.27E-14 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(N[C@@H](Cc1ccccc1)C(O)=O)c2cnccn2
(2) InChI: InChI=1/C14H13N3O3/c18-13(12-9-15-6-7-16-12)17-11(14(19)20)8-10-4-2-1-3-5-10/h1-7,9,11H,8H2,(H,17,18)(H,19,20)/t11-/m0/s1
(3) InChIKey: DWYZPDHMMZGQAP-NSHDSACABA