With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1334177-86-4,1-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)-3-oxo-7,10,13,16,19,22,25,28-octaoxa-4-azahentriacontan-31-oic acid,as a common compound, the synthetic route is as follows.,1334177-86-4
Chloroform (1 0.00 ml) and methanol (0.4 ml) were added to crude 17 (307 mg, 0.254 30 mmol) followed by mal-amido-peg8-acid (339 mg, 0.561 mmol, 2.2 eq) and EDCI (1 07 mg, 0.558 mmol, 2.19 eq). The reaction was allowed to proceed at room temperature for 45 min when completion was observed by LCMS. Ammonium chloride in water (30 ml, 6 mass%) was added and the mixture was stirred vigorously. The mixture was decanted in a biotage phase separation cartridge. The DCM layer was evaporated to dryness under vacuum. 35 The volatiles were removed by rotoevaporation and the crude residue was purified by chromatography (50g Ultra, Biotage, gradient 30/70 to 100/0 of 16% MeOH in DCM I DCMin 1 OCV; Elution at more than 10% of MeOH). All fractions were analysed by TLC (1 0% MeOH in DCM). The pure fractions were pooled. The solvent was removed by evaporation to give 18 (200 mg). LCMS analysis showed traces of mal-pegS-acid, and the material was purified further by preparative HPLC, freeze-dried, aliquoted in dichloromethane, and dried 5 under high vacuum to give 18 as a white solid. The purity was 99.45%. (B, 110 mg, 0.0467 mmol, 18.3% Yield). Analytical Data: LC/MS, 15 min method, RT 5.90 min; MS (ES+) m/z (relative intensity) 1179.5 ([M + 2Hf+¡¤, 100); 1H NMR (400 MHz, DMSO-d6) o 9.92 (s, 2H), 8.16 (d, J = 6.9 Hz, 2H), 7.99 (t, J = 5.7 Hz, 2H), 7.86 (d, J = 8.7 Hz, 2H), 7.55 (s, 4H), 7.18 (s, 4H), 7.07 (s, 2H), 7.00 (s, 4H), 6.79 (s, 2H), 6.50 (s, 2H), 5.48 (s, 2H), 5.23- 4.77 (m, 10 4H), 4.39 (t, J = 7.0 Hz, 2H), 4.22 (dd, J = 8.7, 6.6 Hz, 2H), 4.10 (s, 4H), 3.77 (s, 6H), 3.64 – 3.55 (m, 8H), 3.55- 3.42 (m, 56H), 3.37 (t, J = 5.9 Hz, 6H), 3.28 (t, J = 8.3 Hz, 2H), 3.15 (q, J = 5.8 Hz, 4H), 2.49-2.37 (m, 4H), 2.37-2.30 (m, 4H), 2.17 (s, 2H), 2.09- 1.73 (m, 1 OH), 1.30 (d, J = 7.0 Hz, 6H), 0.85 (dd, J = 15.3, 6.7 Hz, 12H). 15
1334177-86-4 1-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)-3-oxo-7,10,13,16,19,22,25,28-octaoxa-4-azahentriacontan-31-oic acid 51340955, apyrrolines compound, is more and more widely used in various fields.
Reference£º
Patent; MEDIMMUNE LIMITED; DIMASI, Nazzareno; HOWARD, Philip Wilson; MASTERSON, Luke; TIBERGHIEN, Arnaud Charles; VIJAYAKRISHNAN, Balakumar; WHITE, Jason; (135 pag.)WO2019/34764; (2019); A1;,
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