ChemicalBook CAS DataBase List 3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid

3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid synthesis

4synthesis methods

Product Name:3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid
CAS Number:202467-69-4
Molecular formula:C20H19N3O7S
Molecular Weight:445.45

99-05-8

2-Thia-5-azabicyclo[2.2.1]heptane-5-carboxylic acid, 3-oxo-, (4-nitrophenyl)methyl ester, (1S,4S)-

151072-00-3

3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid

202467-69-4

At 60 °C, m-aminobenzoic acid (9.45 g, 68.9 mmol) was dissolved in 200 g of methanol and 1 g of tributylphosphine and 400 ml of a methanolic solution of 4M HCl were added. Subsequently, 220 g of methanol solution of 4-nitrobenzyl (1S,4S)-3-oxo-2-thia-5-azabicyclo[2.2.1]heptane-5-carboxylate (19.8 g, 64.28 mmol) was slowly added. The reaction was stirred at the same temperature for 3 hours. After completion of the reaction, the slurry was cooled and filtered to obtain white crystals. The white crystals were washed with methanol and then dried under vacuum to afford 3-((2S,4S)-4-mercapto-1-(((4-nitrobenzyloxy)oxy)carbonyl)pyrrolidine-2-carboxamido)benzoic acid (127.8 g) in 97% molar yield and 99.2% HPLC purity.

99-05-8
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151072-00-3
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202467-69-4
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Yield:202467-69-4 97%

Reaction Conditions:

with hydrogenchloride;tributylphosphine in methanol at 60; for 3 h;Temperature;Solvent;

Steps:

1 Example 1: Preparation of Compound 1
In 60 °C conditions, containing m-aminobenzoic acid to (9.45g, 68 . 9mmol) methanol solution of 200g in, added tributylphosphine 1g and 4MHCl/methanol solution 400 ml, then slowly adding raw material I (19.8g, 64 . 28mmol) methanol solution of 220g, stirring reaction at the same temperature and 3h, the slurry reaction cooling and filtering, to obtain white crystal, white crystal washing with methanol, vacuum drying, get compound 127.8g, molar yield 97%, HPLC purity 99.2%

References:

Handan Kangrui Biotechnology Co., Ltd;Zhang, Yanling;qin, Yujun;Mi, guorui CN105566193, 2016, A Location in patent:Paragraph 0014; 0015

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51-35-4 Synthesis