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With water; acetic acid; for 3h;Inert atmosphere; Reflux;
(a) (S)-6-Oxo-piperidine-2-carboxylic acid A mixture of (S)-2-amino-hexanedioic acid (50 g, 310.25 mmol), acetic acid (100 mL), and water (400 mL) water was refluxed for 3 h. The unchanged starting amino acid was filtered off (24 g) and the filtrate evaporated, dissolved in hot water (50 mL) and then cooled. A crystalline precipitate formed which was filtered to provide the title intermediate (20 g, 45percent yield).
In ethanol;
Step A. (S)-6-Oxopiperidine-2-carboxylic acid A solution of (S)-2-aminohexanedioic acid (470 mg, 2.9 mmol) in 20percent AcOH (5 mL) was stirred at 110° C. overnight. The solvent was removed in vacuo and the residue was dissolved in EtOH (10 mL). The unreacted amino acid was precipitated and filtered off. The filtrate was concentrated to give the crude desired product which was used directly in the next step. MS: 142.1 (M-1)-.
With acetic acid; at 110℃;
Example 6. Preparation of (S)-N-((S)-l-(2-chlorophenyl)-2-((3,3-difluorocyclobutyl) - amino)-2-oxoethyl)-N-(3-fluorophenyl)-6-oxo-l-(pyrimidin-2-yl)piperidine-2-carboxamide Compounds 19 and 20 were prepared according to the following scheme, using the following protocol. Step A. (S)-6-Oxopiperidine-2-carboxylic acid. A solution of (S)-2-aminohexanedioic acid (470 mg, 2.9 mmol) in 20percent AcOH (5 niL) was stirred at 1 10 °C overnight. The solvent was removed in vacuo and the residue was dissolved in EtOH (10 mL). The unreacted amino acid was precipitated and filtered off. The filtrate was concentrated to give the crude desired product which was used directly in the next step. MS: 142.1 (M-l)\
With acetic acid; at 110℃;
A solution of (S)-2-aminohexanedioic acid (470mg, 2.9 mmol) in 20percent AcOH (5 mL) was stirred at 110 °C overnight. The solvent was removed in vacuo and the residue was dissolved in EtOH (lOmL). The unreacted amino acid was precipitated and filtered off. The filtrate was concentrated to give the crude desired product which was used directly in the next step. MS: 142.1 (M-1).
With acetic acid; at 110℃;
Step A. (S)-6-Oxopiperidine-2-carboxylic acid. A solution of (S)-2-aminohexanedioic acid (470 mg, 2.9 mmol) in 20percent AcOH (5 mL) was stirred at 1 10 °C overnight. The solvent was removed in vacuo and the residue was dissolved in EtOH ( 10 mL). The unreacted amino acid was precipitated and filtered off. The filtrate was concentrated to give the crude desired product which was used directly in the next step. MS: 142. 1 (M- l )'.
(S)-4-Guanidino-2-[((S)-1-{(S)-5-guanidino-2-[(S)-2-((S)-4-methyl-2-{(S)-2-[((S)-6-oxo-piperidine-2-carbonyl)-amino]-3-phenyl-propionylamino}-pentanoylamino)-3-phenyl-propionylamino]-pentanoyl}-pyrrolidine-2-carbonyl)-amino]-butyric acid[ No CAS ]
[ 1118-90-7 ]
[ 34622-39-4 ]
(S)-2-[(S)-1-((S)-2-{(S)-2-[(S)-2-((S)-2-Amino-3-phenyl-propionylamino)-4-methyl-pentanoylamino]-3-phenyl-propionylamino}-5-guanidino-pentanoyl)-pyrrolidine-2-carbonyl]-amino}-4-guanidino-butyric acid[ No CAS ]
(S)-5-Amino-5-{(S)-1-[(S)-1-((S)-1-{(S)-1-[(S)-2-((S)-1-carboxy-3-guanidino-propylcarbamoyl)-pyrrolidine-1-carbonyl]-4-guanidino-butylcarbamoyl}-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-2-phenyl-ethylcarbamoyl}-pentanoic acid[ No CAS ]
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