Related Products of 23377-40-4 ,Some common heterocyclic compound, 23377-40-4, molecular formula is C19H40O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
Example 12 Ethyl 3-(hexadecyloxy)propyl {3-[({4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7- yl}methyl)amino]propyl}phosphonate (65), Scheme 12Scheme 12 (3-{[(Benzyloxy)carbonyl]amino}propyl)(ethoxy)phosphinic acid (56) (0.52 g) is evaporated twice with MeCN then dissolved in dry DCM (5 mL) and dry DMF (5 pL). This solution is then added to oxalyl chloride (574 muIota, 5 eq.) in dry DCM (5 mL) under Ar, stirred at room temperature for 2 h and then evaporated twice from dry DCM. The resulting crude phosphonyl chloride (57) in dry DCM (5 mL) is added to a solution of 3- hexadecyloxypropan-1-ol (504 mg, 1.3 eq.) and dry pyridine (1 mL) in dry DCM (3 mL). The mixture is stirred at room temperature for 3 h and then treated with saturated sodium bicarbonate solution, extracted with DCM, dried and evaporated. Flash chromatography (hexanes- EtOAc, followed by 5% v/v MeOH in EtOAc) gives benzyl N-(3-{ethoxy[3- (hexadecyloxy)propoxy]phosphoryl}propyl)carbamate (62) (110 mg). 1H NMR (500 MHz, CDCI3) delta 7.36-7.26 (m, 5H), 5.09 (s, 2H), 4.12-4.08 (m, 2H), 3.49-3.47 (m, 2H), 3.40-3.37 (m, 2H), 3.32-3.25 (m, 2H), 1.92-1.89 (m, 2H), 1.79-1.75 (m, 2H), 1.58-1.54 (m, 2H), 1.32-1.25 (m, 30H), 0.89-0.87(m, 3H). 3C NMR (125MHz, CDCI3) delta 156.4,136.6,128.5, 128.1 , 71.2, 66.6, 62.9, 61.7, 31.9, 30.9, 29.7, 29.5, 29.3, 26.2, 22.7, 16.4, 14.1. 31P NMR (202 MHz, CDCI3 ) delta 31.7. ESI-HRMS for C32H58N06PNa [M+Na]+ calcd 606.3899; found 686.3904.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,23377-40-4, its application will become more common.
Reference:
Patent; INDUSTRIAL RESEARCH LIMITED; ALBERT EINSTEIN COLLEGE OF MEDICINE OF YESHIVA UNIVERSITY; CLINCH, Keith; CRUMP, Douglas Ronald; EVANS, Gary Brian; HAZLETON, Keith Zachary; MASON, Jennifer Mary; SCHRAMM, Vern L.; TYLER, Peter Charles; WO2012/150866; (2012); A1;,
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