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(6S,7S)-3-(5-Carboxymethyl-4-methyl-thiazol-2-ylsulfanylmethyl)-7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-8-oxo-4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester[ No CAS ]
(6R,7R)-7-{2-[(Z)-2-(Acetyl-hydroxy-amino)-ethoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-3-(5-carboxymethyl-4-methyl-thiazol-2-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid[ No CAS ]
Reference Example 42; Methyl (4-methyl-2-mercapto-1,3-thiazol-5-yl)acetate [] To a solution of (4-methyl-2-mercapto-1,3-thiazol-5-yl) acetic acid (10 g) in methanol (200 ml) was added concentrated sulfuric acid (0.5 ml) and the mixture was heated under reflux overnight. After methanol was distilled off under reduced pressure, the reaction mixture was diluted with ethyl acetate and washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue was purified by recrystallization (hexane - ethyl acetate) to obtain an objective product (7.18 g) as crystals. Melting point 139 - 140C; 1H-NMR (CDCl3) delta 2.18 (3H, s), 3.51 (2H, s), 3.74 (3H, s), 12.15 (1H, br s).
With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; for 20h;Combinatorial reaction / High throughput screening (HTS);
Each resin from Step 3 was distributed into 24 fritted syringes (Torvig, 50 mg each, 50 mumol), for a total of 96 syringes, and was swelled in NMP (1 mL) for 30 min. The solvent was removed by filtration. Twenty-four solutions of the building blocks listed below (10 mmol each) and DIBA (3.5 mL, 20 mmol) in NMP (10 mL) were prepared. 3 mL of the 24 solutions was added to the 24 syringes for each resin from Step 3, accordingly. The suspensions were then shaken for 20 h on a Titer Plate Shaker. The reaction mixture was filtered and washed 5 times with methylene chloride (5 mL), 3 times with THF (5 mL), 3 times THF/H2O (3/1 v/v, 5 mL), and 3 times with THF (5 mL). The resins were then dried overnight under vacuum.
With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; for 20h;Combinatorial reaction / High throughput screening (HTS);
Each resin from Step 3 was distributed into 24 fritted syringes (Torvig, 50 mg each, 50 mumol), for a total of 96 syringes, and was swelled in NMP (1 mL) for 30 min. The solvent was removed by filtration. Twenty-four solutions of the building blocks listed below (10 mmol each) and DIBA (3.5 mL, 20 mmol) in NMP (10 mL) were prepared. 3 mL of the 24 solutions was added to the 24 syringes for each resin from Step 3, accordingly. The suspensions were then shaken for 20 h on a Titer Plate Shaker. The reaction mixture was filtered and washed 5 times with methylene chloride (5 mL), 3 times with THF (5 mL), 3 times THF/H2O (3/1 v/v, 5 mL), and 3 times with THF (5 mL). The resins were then dried overnight under vacuum.
With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; for 20h;Combinatorial reaction / High throughput screening (HTS);
Each resin from Step 3 was distributed into 24 fritted syringes (Torvig, 50 mg each, 50 mumol), for a total of 96 syringes, and was swelled in NMP (1 mL) for 30 min. The solvent was removed by filtration. Twenty-four solutions of the building blocks listed below (10 mmol each) and DIBA (3.5 mL, 20 mmol) in NMP (10 mL) were prepared. 3 mL of the 24 solutions was added to the 24 syringes for each resin from Step 3, accordingly. The suspensions were then shaken for 20 h on a Titer Plate Shaker. The reaction mixture was filtered and washed 5 times with methylene chloride (5 mL), 3 times with THF (5 mL), 3 times THF/H2O (3/1 v/v, 5 mL), and 3 times with THF (5 mL). The resins were then dried overnight under vacuum.
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