Carbpenem penicillin ertapenem intermediate, and preparation and use thereof
A technology of carbapenems and ertapenem, which is applied in the field of organic compound synthesis, can solve problems such as difficult industrial production, high equipment requirements, and harsh conditions, and achieve the effects of simple operation, high purity, and mild reaction conditions
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Embodiment 1
[0028] Example 1 Synthesis of 4-methoxybenzyl 3-nitrobenzoate (formula II)
[0029] Formula I compound (4.00g, 23.93mmol) in CH 2 Cl 2 50ml, add NEt 3 (4.84g, 47.91mmol), 4-methoxybenzyl chloride (PMBCl) (5.62g, 35.89mmol) was added dropwise at room temperature, the temperature was raised to 45°C, and the reaction was carried out for 3 hours. use CH 2 Cl 2 and water extraction, combined CH 2 Cl 2 layer with anhydrous NaSO 4 Dry, filter, and concentrate the filtrate to obtain a light yellow solid (Formula II) (6.29 g, yield 91.5%, purity >99%). Melting point: 82-84°C. The identification results are as follows:
[0030] NMR (CDCl 3 )δ: 3.81(s, 3H); 5.35(s, 2H); 6.93(m, 2H); 7.40(m, 2H); 7.63(m, 1H); )
[0031] MS (CI): 287
Embodiment 2
[0032] Example 2 Synthesis of 4-methoxybenzyl 3-nitrobenzoate (formula II)
[0033] Formula I compound (150.00g, 0.898mol) in ethyl acetate 100ml, add NEt 3 (181.89g, 1.797mol), PMBCl (251.49g, 1.605mol) was added dropwise at room temperature, the temperature was raised to 60°C, and the reaction was carried out for 5 hours. use CH 2 Cl 2 and water extraction, combined CH 2 Cl 2 layer with anhydrous NaSO 4 Dry, filter, and concentrate the filtrate to obtain a light yellow solid, which is recrystallized from ethanol to obtain white crystals (Formula II) (256.53 g, yield 99.5%, purity 100%). Melting point: 83-85°C. Identification result is the same as embodiment 1.
Embodiment 3
[0034] Example 3 Synthesis of 4-methoxybenzyl 3-nitrobenzoate (formula II)
[0035] Formula I compound (150.00g, 0.898mol) was added to 200ml of toluene, pyridine (106.41g, 1.35mol) was added, PMBCl (422.13g, 2.694mol) was added dropwise at room temperature, the temperature was raised to 40°C, and the reaction was carried out for 10 hours. use CH 2 Cl 2 and water extraction, combined CH 2 Cl 2 layer with anhydrous NaSO 4 Dry, filter, and concentrate the filtrate to obtain a light yellow solid, which is recrystallized from ethanol to obtain white crystals (Formula II) (256.00 g, yield 99.1%, purity >99%). Melting point: 83-85°C. Identification result is the same as embodiment 1.
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