In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, tert-Butyl 3-iodobenzylcarbamate, other downstream synthetic routes, hurry up and to see.
Adding a certain compound to certain chemical reactions, such as: 263351-43-5, name is tert-Butyl 3-iodobenzylcarbamate, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 263351-43-5, Safety of tert-Butyl 3-iodobenzylcarbamate
tert-Butyl [3-[5-[[1-(Benzyloxycarbonyl)-2(S)-azetidinyl]methoxy]-3-pyridyl]benzyl]carbamate 3-[[1-(Benzyloxycarbonyl)-2(S)-azetidinyl]methoxy]-5-(trimethylstannyl)pyridine (682 mg, 1.48 mmol), tert-butyl 3-iodobenzylcarbamate (498 mg, 1.48 mmol), and anhydrous DMF (5 mL) were placed in a 50 mL round-bottom flask with magnetic stirrer. To this mixture were added rapidly CsF (450 mg, 2.96 mmol, 2 equiv.), CuI (29 mg, 0.15 mmol, 0.1 equiv.), and tetrakis(triphenylphosphine)palladium(0) (87 mg, 75 mumol, 0.05 equiv.). The flask was fitted with a three-way stopcock with argon balloon, and the atmosphere was exchanged. The reaction mixture was heated at 50 C. for 6 h, during which time it turned from an olive-colored solution to a dark suspension. The solvent was pumped off at 30 C. with an oil pump into a -78 C. receiver. The residue was stirred with ether (20 mL) to disperse the solid, which was then removed by suction filtration over celite. The filter residue was twice washed with ether (15 mL each), and the combined ether solutions were evaporated. TLC (SiO2, EtOAc) showed the formation of a major product at Rf 0.5 (UV- and KMnO4-active) followed by residual DMF (Rf 0.15; KMnO4 stain only). The crude product was chromatographed on silica gel (20*3.8 cm) with a stepwise gradient of EtOAc/hexane 1:1, 2:1, 3:1, and 4:1. The product-containing eluate fractions were evaporated. The residue was taken up in DMSO (2.2 mL) and further purified by preparative HPLC in a single portion on a Supelco Discovery C18 column (250*21.2 mm, 5 mum particle size; UV detection at 270 nm; flow/solvent gradient: 0-12 min, 6 to 12.5 mL/min (then remaining at this value)/20% CH3CN in water; 20-100% within 40 min; run aborted after elution of the main peak and column washed with CH3CN). The product eluted at tR 39.8-41.9 min. Evaporation and drying (50 C./oil pump) gave 542 mg (73%) of a yellowish glass. [alpha]D -44.3, [alpha]546 -52.5 (c 10.5 g/L, EtOAc). 1H NMR (CDCl3, 500 MHz) delta 8.48 (s, 1H), 8.32 (br, 1H), 7.51-7.25 (m, 10H), 5.13, 5.09 (ABq, 2H, J=12.4 Hz), 4.96 (br, 1H), 4.67 (br, 1H), approx. 4.5 (very br, 1H), 4.42 (br d, 2H, J=5.3 Hz), 4.22 (br, 1H), 4.08-4.00 (m, 2H), 2.51-2.32 (m, 2H), 1.50 (s, 9H). MS (EI) m/z 503 (M+, 0.6%), 447 (1.5%), 312 (2.4%), 199 (2.6%), 91 (100%), 57 (18%).
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, tert-Butyl 3-iodobenzylcarbamate, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; The Board of Trustees of the University of Illinois; PsychoGenics, Inc.; Chandrasekhar, Jayaraman; Kozikowski, Alan P.; Liu, Jianhua; Tueckmantel, Werner; Walker, Joel R.; Yuen, Po-wai; US2013/184313; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com