(S)-3-PHENYL-2-[(PYRAZIN-2-YLCARBONYL)AMINO] PROPANOIC ACID synthesis
- Product Name:(S)-3-PHENYL-2-[(PYRAZIN-2-YLCARBONYL)AMINO] PROPANOIC ACID
- CAS Number:114457-94-2
- Molecular formula:C14H13N3O3
- Molecular Weight:271.27
73058-37-4
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114457-94-2
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Yield:114457-94-2 93.6%
Reaction Conditions:
with sodium hydroxide in acetone; pH=12 - Ca. 13Cooling with ice;
Steps:
3 Preparation example 3 N-pyrazineformyl-L-phenylalanine
The product N-pyrazineformyl-L-phenylalanine methyl ester (1.0g, 3.51mmol) in Preparation example 2 was dissolved with 10ml of acetone, 2N NaOH was added dropwise slowly until a pH value of 12～13 was obtained, and the solution was kept reacting under the condition of ice water bath, the reaction was monitored by TLC and completed after 2h.
Hydrochloric acid was add dropwise under the condition of ice water bath until a pH value of 2～3 was obtained, a large amount of white solid was produced, the generated precipitate was filtered, washed with water and diethyl ether followed by airing to dry and gave 0.89g of white product with a yield of 93.6%, m.p.: 166-169°C. 1H-NMR (DMSO-d6, 300MHz): 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:
Peking University;LI, Runtao;CUI, Jingrong;ZHU, Yongqiang;YAO, Shuyang;GE, Zemei;CHENG, Tieming EP2444411, 2016, B1 Location in patent:Paragraph 0038
19847-10-0
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63-91-2
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114457-94-2
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7364-51-4
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103435-88-7
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114457-94-2
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7524-50-7
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114457-94-2
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$5.00/250mg