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

Product Name
(S)-3-PHENYL-2-[(PYRAZIN-2-YLCARBONYL)AMINO] PROPANOIC ACID
CAS No.
114457-94-2
Chemical Name
(S)-3-PHENYL-2-[(PYRAZIN-2-YLCARBONYL)AMINO] PROPANOIC ACID
Synonyms
N-PyrazinyL;Bortezomib INT;Bortezomib INT B;Bortezomib impurity B;Bortezomib Acid Analog;Bortezomib impurity 92;Antibacterial agent 268;N-(2-pyrazinylcarbonyl)-;Bortezomib Acid Impurity;Bortezomib Intermediate 2
CBNumber
CB41119462
Molecular Formula
C14H13N3O3
Formula Weight
271.27
MOL File
114457-94-2.mol
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(S)-3-PHENYL-2-[(PYRAZIN-2-YLCARBONYL)AMINO] PROPANOIC ACID Property

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
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Safety

HS Code 
2933998090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TCI Chemical
Product number
P2068
Product name
N-(Pyrazinylcarbonyl)-L-phenylalanine
Purity
>98.0%(HPLC)
Packaging
1g
Price
$50
Updated
2025/07/31
TRC
Product number
P841500
Product name
N-Pyrazinylcarbonyl-L-phenylalanine
Packaging
250mg
Price
$95
Updated
2021/12/16
Usbiological
Product number
287137
Product name
N-Pyrazinylcarbonyl-L-phenylalanine
Packaging
100mg
Price
$305
Updated
2021/12/16
Activate Scientific
Product number
AS80282-2S
Product name
(S)-3-Phenyl-2-(pyrazine-2-carboxamido)propanoic acid
Purity
98% ee
Packaging
5G
Price
$549
Updated
2021/12/16
Apolloscientific
Product number
OR302741
Product name
(S)-3-Phenyl-2-(pyrazine-2-carboxamido)propanoicacid
Packaging
5g
Price
$653
Updated
2021/12/16
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(S)-3-PHENYL-2-[(PYRAZIN-2-YLCARBONYL)AMINO] PROPANOIC ACID Chemical Properties,Usage,Production

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

73058-37-4

114457-94-2

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 Preparation Products And Raw materials

Raw materials

Preparation Products

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

Canada 3 China 281 France 1 Germany 1 India 22 Japan 1 Russia 1 Switzerland 1 United Kingdom 4 United States 22 Global 337
CMS Chemicals Limited
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Manchester Organics
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Biosynth Carbosynth
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Apollo Scientific Ltd.
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View Lastest Price from (S)-3-PHENYL-2-[(PYRAZIN-2-YLCARBONYL)AMINO] PROPANOIC ACID manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
(S)-3-phenyl-2-(pyrazine-2-carboxamido)propanoic acid 114457-94-2
Price
US $0.00-0.00/Kg/Drum
Min. Order
1KG
Purity
99%min
Supply Ability
1000 KGS
Release date
2021-06-19
Hebei Zhuanglai Chemical Trading Co Ltd
Product
(S)-3-PHENYL-2-[(PYRAZIN-2-YLCARBONYL)AMINO] PROPANOIC ACID 114457-94-2
Price
US $10.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20 ton
Release date
2024-12-10
Henan Aochuang Chemical Co.,Ltd.
Product
(S)-3-PHENYL-2-[(PYRAZIN-2-YLCARBONYL)AMINO] PROPANOIC ACID 114457-94-2
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1ton
Release date
2022-10-13

114457-94-2, (S)-3-PHENYL-2-[(PYRAZIN-2-YLCARBONYL)AMINO] PROPANOIC ACIDRelated Search:

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

  • (S)-3-PHENYL-2-[(PYRAZIN-2-YLCARBONYL)AMINO] PROPANOIC ACID
  • (S)-3-Phenyl-2-[(pyrazine-2-carbonyl)-amino]-propionic acid
  • Bortezomib Intermediate 2
  • N-Pyrazinylcarbonyl-L-phenylalanine
  • N-(2-Pyrazinylcarbonyl)-L-phenylalanine
  • Bortezomib Acid Impurity
  • Bortezomib INT B
  • <i>N</i>-(Pyrazinylcarbonyl)-<small>L</small>-phenylalanine
  • (S)-3-Phenyl-2-(pyrazine-2-carboxaMido)propanoic acid
  • N-(2-pyrazinylcarbonyl)-
  • BortezoMib IMpurity B ((S)-3-Phenyl-2-(pyrazine-2-carbonylaMino)propanoic Acid)
  • L-Phenylalanine, N-(2-pyrazinylcarbonyl)-
  • Bortezomib impurity B
  • Bortezomib INT
  • Bortezomib impurity 12/((S)-3-Phenyl-2-(pyrazine-2-carbonylamino)propanoic Acid
  • (2S)-3-phenyl-2-[(pyrazin-2-yl)formamido]propanoic acid
  • (pyrazine-2-carbonyl)-L-phenylalanine
  • (S)-3-Phenyl-2-(pyrazine-2-carbox
  • 2-[[oxo(2-pyrazinyl)methyl]amino]-3-phenylpropanoic acid
  • N-PyrazinyL
  • Bortezomib USP Impurity D
  • N-((S)-1-(((S)-3-methyl-1-((3aR,4R,6R,7aS)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)amino)-1-oxo-3- phenylpropan-2-yl)pyrazine-2-carboxamide
  • (S)-3-Phenyl-2-[[(pyrazin-2-yl)carbonyl]amino]propanoic acid (Bortezomib Impurity)
  • Bortezomib Related Compund D/ Bortezomib Acid Analog
  • (R)-3-methyl-1-((3aS,4S,6S,7aS)-3a,5,5- trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butan-1- amine
  • Bortezomib Acid Analog
  • (S)-3-Phenyl-2-(pyrazine-2-carboxamido)propanoicaci
  • (S)-3-phenyl-2-(pyrazine-5-carboxamido)propanoic acid
  • (S)-3-Phenyl-2-(pyrazine-2-carboxamido)propanoic acid|||N-(Pyrazinylcarbonyl)-L-phenylalanine
  • Bortezomib impurity 92
  • Antibacterial agent 268
  • (S)-3-Phenyl-2-[(pyrazine-2-carbonyl)amino]propanoicacid
  • (S)-3-Phenyl-2-(pyrazine-2-carboxcarboxamido)-propanoic acid
  • 114457-94-2
  • 114459-94-2
  • 1144557-94-2
  • Amino Acids & Derivatives
  • Aromatics