| Identification | Back Directory | [Name]
(S)-3-PHENYL-2-[(PYRAZIN-2-YLCARBONYL)AMINO] PROPANOIC ACID
| [CAS]
114457-94-2 | [Synonyms]
N-PyrazinyL
Bortezomib INT
Bortezomib INT B
Bortezomib impurity B
N-(2-pyrazinylcarbonyl)-
Bortezomib Acid Impurity
Bortezomib Intermediate 2
Bortezomib USP Impurity D
(S)-3-Phenyl-2-(pyrazine-2-carbox
N-Pyrazinylcarbonyl-L-phenylalanine
(pyrazine-2-carbonyl)-L-phenylalanine
N-(2-Pyrazinylcarbonyl)-L-phenylalanine
L-Phenylalanine, N-(2-pyrazinylcarbonyl)-
Bortezomib Related Compund D/ Bortezomib Acid Analog
(S)-3-Phenyl-2-(pyrazine-2-carboxaMido)propanoic acid
(2S)-3-phenyl-2-[(pyrazin-2-yl)formamido]propanoic acid
2-[[oxo(2-pyrazinyl)methyl]amino]-3-phenylpropanoic acid
N-(Pyrazinylcarbonyl)-L-phenylalanine
(S)-3-Phenyl-2-[(pyrazine-2-carbonyl)-amino]-propionic acid
(S)-3-PHENYL-2-[(PYRAZIN-2-YLCARBONYL)AMINO] PROPANOIC ACID
Bortezomib impurity 12/((S)-3-Phenyl-2-(pyrazine-2-carbonylamino)propanoic Acid
BortezoMib IMpurity B ((S)-3-Phenyl-2-(pyrazine-2-carbonylaMino)propanoic Acid)
(S)-3-Phenyl-2-[[(pyrazin-2-yl)carbonyl]amino]propanoic acid (Bortezomib Impurity)
(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
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 | [Molecular Formula]
C14H13N3O3 | [MDL Number]
MFCD09800536 | [MOL File]
114457-94-2.mol | [Molecular Weight]
271.271 |
| Chemical Properties | Back Directory | [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) | [form ]
Solid | [pka]
13.93±0.46(Predicted) | [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 |
| Hazard Information | Back Directory | [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 |
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