Carbapenem 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, low cost, and mild reaction conditions
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[0051] Reference Examples Preparation of Formula V Compounds
[0052] Formula I compound (26.5g, 157.9mmol) in CH 2 Cl 2 350ml, add NEt 3 (32g, 316.1mmol), 4-methoxybenzyl chloride (PMBCl) (44.4g, 283.6mmol) 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) (41.5 g, yield 91.5%, purity >99%).
[0053] Compound shown in formula II (40.93g, 142.47mmol) in SnCl 2· 2H 2 O (161.0 g, 712.37 mmol) in 300 ml of ethanol was heated up to 50° C. and reacted until all solids were dissolved. Adjust the pH to 11 with 15% NaOH alcohol solution, extract with ether and water, combine the ether layers, anhydrous NaSO 4 Dry, filter, and concentrate the filtrate to obtain a light yellow solid (Formula III) (33.84 g, 92.3%).
[0054] PNZ L-Hydroxyp...
Embodiment 1
[0057] Compound of formula V (5.00g, 7.97mmol) was dissolved in DMF20ml, toluene 20ml, potassium thioacetate (AcSK) (4.09g, 35.86mmol) was added, heated to 55°C, and reacted for 8h. Extract with EA and water, combine the ethyl acetate layers, concentrate, and recrystallize the brown semi-solid from ethyl acetate and n-hexane to obtain the product (formula VI) (3.6 g, yield 74%). Melting point: 140-142°C. The identification results are as follows:
[0058] NMR (CDCl 3 )δ: 2.25(s, 3H); 2.50(m, 2H); 2.87(m, 1H); 3.78(s, 3H); 4.10(m, 1H); 4.30(m, 2H); ); 5.45(s, 2H); 6.68(m, 2H); 7.10(m, 2H), 7.30(m, 1H); 7.40(m, 2H); 7.67(m, 1H); 7.80(m, 1H) ;8.05(s,1H);8.18(m,2H);8.30(s,1H)
[0059] MS(CI):629.9(M+Na)
Embodiment 2
[0061] The compound of formula V (34.00g, 54.59mmol) was dissolved in 120ml of DMF and 100ml of ethyl acetate, and AcSK (22g, 192.78mmol) was added, heated to 58°C, and reacted for 5h. Extract with ethyl acetate and water, combine the ethyl acetate layers, concentrate, and wash the brown semi-solid with methanol to obtain the product (formula VI) (29 g, yield 88%). Melting point: 144-145°C. Identification result is the same as embodiment 1.
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