(S)-3-PHENYL-2-[(PYRAZIN-2-YLCARBONYL)AMINO] PROPANOIC ACID Chemical Properties

Melting point:

166-169℃

Boiling point:

573.8±50.0 °C(Predicted)

Density 

1.323

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO, Methanol (Sparingly)

pka

13.93±0.46(Predicted)

form 

Solid

color 

White to Light Beige

InChI

InChI=1S/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

InChIKey

DWYZPDHMMZGQAP-NSHDSACASA-N

SMILES

C(O)(=O)[C@H](CC1=CC=CC=C1)NC(C1=NC=CN=C1)=O

Safety Information

HS Code 

2933998090

(S)-3-PHENYL-2-[(PYRAZIN-2-YLCARBONYL)AMINO] PROPANOIC ACID Usage And Synthesis

Chemical Properties

(S)-3-PHENYL-2-[(PYRAZIN-2-YLCARBONYL)AMINO] PROPANOIC ACID is Light Beige Solid

Uses

(S)-3-PHENYL-2-[(PYRAZIN-2-YLCARBONYL)AMINO] PROPANOIC ACID is used for the synthesis of Bortezomib (B675700) from L-phenylalanine via dipeptidyl boronic acid ester intermediates.

Synthesis

General procedure for the synthesis of (S)-3-phenyl-2-(pyrazine-2-carboxamido)propionic acid from (pyrazine-2-carbonyl)-L-phenylalanine methyl ester: N-pyrazinecarbonyl-L-phenylalanine methyl ester (1.0 g, 3.51 mmol) was dissolved in 10 mL of acetone, and the pH was adjusted to 12-13 by slowly adding 2N NaOH solution dropwise under cooling in an ice-water bath.Reaction. The progress of the reaction was monitored by thin-layer chromatography (TLC) during the process, and the reaction was completed after 2 hours. Subsequently, hydrochloric acid was slowly added dropwise in an ice-water bath and the pH was adjusted to 2~3, at which time a large amount of white solid precipitated. The precipitate was collected by filtration, washed with water and ether sequentially, and then dried in air. Finally, 0.89 g of white solid product was obtained with a yield of 93.6% and a melting point of 166-169°C. The product structure was analyzed by 1H-NMR. The structure of the product was confirmed by 1H-NMR (DMSO-d6, 300 MHz): δ 3.23 (-CH2, m, 2H), 4.74 (-CH, m, 1H), 7.16-7.25 (-Ph, m, 5H), 8.74 (-CONH, t, 1H), 8.86-8.89 (-Pyz, t, 2H), 9.14 (-Pyz. d, 1H), 13.06 (-COOH, s, 1H).

References

[1] Patent: EP2444411, 2016, B1. Location in patent: Paragraph 0038
[2] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 15, p. 4031 - 4044
[3] Organic and Biomolecular Chemistry, 2007, vol. 5, # 9, p. 1416 - 1426
[4] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 19, p. 6851 - 6861
[5] Journal of Medicinal Chemistry, 2009, vol. 52, # 14, p. 4192 - 4199

(S)-3-PHENYL-2-[(PYRAZIN-2-YLCARBONYL)AMINO] PROPANOIC ACID(114457-94-2)Related Product Information

• Palladium (II) Acetate
• Phosphorus trichloride
• Ufiprazole
• Sildenafil citrate
• 2-PyrazinecarboxaMide, N-[(1S)-2-[[(1R)-1-hydroperoxy-3-Methylbutyl]aMino]-2-oxo-1-(phenylMethyl)ethyl]-
• L-Phenylalanine
• BortezoMib IMpurity N
• 1-Chloro-2-methylpropane
• Bortezomib Impurity 45
• BOC-D-Phenylalanine
• N-((S)-1-(((S)-1-Hydroxy-3-Methylbutyl)aMino)-1-oxo-3-phenylpropan-2-yl)pyrazine-2-carboxaMide
• Sildenafil
• ((R)-3-Methyl-1-((R)-3-phenyl-2-(pyrazine-2-carboxaMido)propanaMido)butyl)boronic acid
• (aR,3aS,4S,6S,7aR)-Hexahydro-3a,8,8-trimethyl-alpha-(2-methylpropyl)-4,6-methano-1,3,2-benzodioxaborole-2-methanamine 2,2,2-trifluoroacetate
• ((S)-3-Methyl-1-((S)-3-phenyl-2-(pyrazine-2-carboxaMido)propanaMido)butyl)boronic acid
• Boronic acid, B-[(1S)-3-Methyl-1-[[(2R)-1-oxo-3-phenyl-2-[(2-pyrazinylcarbonyl)aMino]propyl]aMino]butyl]-
• Bortezomib
• Bortezomib Impurity 5