55750-48-6 Methyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate 580610, apyrrolines compound, is more and more widely used in various.
With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.55750-48-6,Methyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate,as a common compound, the synthetic route is as follows.
Compound 42 (160 mg, 0.17 mmol, 1 eq.) was dissolved in a mixture of THF (5 ml) and a saturated NaHC03solution (1 ml), cooled to 0C in an ice bath and maleimide- carbamate 22 (26 mg, 0.17 mmol, 1 eq.) was added. The mixture was stirred for 30 min. Then, Na2C03(1 M in H20) (169 mu, 0.17 mmol, 1 eq.) was added and stirred for an additional 45 min. Then, H20 was added to the mixture, extracted twice with EtOAc and dried on MgS04. The solution was filtered and concentrated in vacuo followed by purification of the crude product by silica gel column chromatography (DCM/MeOH, 1:0 to 95:5 v/v) to yield compound 43 (100 mg, 0.10 mmol, 58%) as a white waxy solid.1H NMR (DMSO-d6, 400 MHz): delta = 1.31-1.45 (9H, m, CH3,Boc), 2.76-2.95 (6H, m, ArCH3, NCH3), 3.41 (3H, s, OCH3), 3.40-3.79 (21H, m, CHC1, NCH2, OCH2), 3.79-3.85(1H, m, CHC1), 4.46 (1H, t, HI), 4.63-4.70 (1H, m, H2), 5.16-5.21 (1H, m, H2), 5.30 (2H, s, OCH20), 6.99 (2H, d, HC=CH), 7.11-7.27 (4H, d, H3″), 7.32-7.43 (2H, m, H7, H8), 7.56- 7.60 (1H, m, H8′), 7.68-7.84 (2H, m, H6, H7′), 7.99 (2H, d, H2″), 8.35 (1H, br s, H4), 8.69 (1H, s, H3′), 9.47 (1H, s, H5′), 10.31 (1H, s, Ar-NHC(O)-Ar).13C NMR (DMSO-d6, 100 MHz): delta = 22.9 (Ar-CH3), 28.5, 28.6 (CH3, Boc), 34.5(NCH3), 37.2, 37.3 ((C=0)2N H2CH2), 44.7 (CI), 45.5, 46.0, 46.4, 47.5 (NCH2), 47.9 (CH2C1), 55.1 (C2), 56.3 (OCH3), 67.4, 67.4, 68.5, 69.1, 69.9, 69.9, 70.2, 70.2, 70.3,70.4 (OCH2), 79.1, 79.1 (CBoc), 94.2 (OCH20), 111.0, 111.1 (C4), 116.2 (C3″), 117.8 (C5′), 118.0 (C7), 119.5 (C3′), 121.2, 121.3 (C6), 122.8 (C9b), 123.6 (C8′), 125.1 (C7), 126.3 (C5a), 127.8 (C6′), 127.9 (CI”), 130.1 (C2″), 130.3 (C9a), 131.0 (C8), 133.5 (C9), 135.0 (HC=CH), 141.0 (C2′), 141.9 (C8a’), 142.4 (C3a), 148.5, 148.6 (Ar-OC(O)N), 154.3 (C5), 155.2, 155.5MS (ESI) m z; calculated: 1026.40 [M+H]+, found: 1026.59 [M+H]+
55750-48-6 Methyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate 580610, apyrrolines compound, is more and more widely used in various.
Reference£º
Patent; SYNTHON BIOPHARMACEUTICALS B.V.; ELGERSMA, Ronald Christiaan; HUIJBREGTS, Tijl; COUMANS, Rudy Gerardus Elisabeth; (112 pag.)WO2018/69375; (2018); A1;,
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