6249-56-5 3-Carboxy-N,N,N-trimethylpropan-1-aminium chloride 22620, acatalyst-ligand compound, is more and more widely used in various fields.
With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6249-56-5,3-Carboxy-N,N,N-trimethylpropan-1-aminium chloride,as a common compound, the synthetic route is as follows.
6249-56-5, Example 620-Oxo-5p-pregnan-3a-yl 4-(trimethylammonium) butanoate chloride3-Carboxy-N,N,N-trimethylpropan-l -ammonium chloride (prepared according to Lindstedt and Lindstedt, 1965, 69 mg; 0.38 mmol) was suspended in anhydrous CH2C12 (1 mL) under argon. The reaction flask was cooled in ice bath and oxalyl chloride (0.5 mL; 5.82 mmol) was added dropwise, followed by catalytic amount of dry DMF (3 mu; 0.03 mmol). The heterogeneous mixture was then brought to r.t. and stirred for 16 hrs, during which all the solids dissolved. The mixture was evaporated under the reduced pressure and solid residue was dissolved in dry nitromethane (2 mL) and dry pyridine (0.10 mL; 1.24 mmol) under argon. Compound II (100 mg; 0.31 mmol) was added to this reaction mixture, which was then stirred for 4 hrs. Reaction was quenched with water (10 mL) and acidified to pH 4 with 5percent aq. HC1. Product was extracted with CHC13 (3 x 20 mL), solution was washed with brine (10 mL, dried with anhydrous MgS04 and evaporated under the reduced pressure. Trituration with benzene removed the unreacted starting steroide II and the remaining product was subsequently crystallized from CHC13 : n-heptane (1 : 1) to give needle-like crystals (134 mg; 89percent).[a]D = +88.4 (c 0.243); NMR (500 MHz, CDC13) delta 4.76-4.68 (m, 1H, 3-CH), 3.73-3.73 (bm, 2H, 4′-CH2), 3.47 (s, 9H, NCH3), 2.55 (t, 1H, J = 9.0 Hz, 17-CH), 2.49 (t, 2H, J = 6.2 Hz, 2′-CH2), 2.12 (s, 3H, 21- CH3), 0.94 (s, 3H, 19-CH3), 0.60 (s, 3H, 18-CH3). 13C NMR (101 MHz, CDC13) delta 209.47, 171.49, 75.20, 65.61, 63.79, 56.62, 53.45, 44.26, 41.83, 40.41, 39.13, 35.76, 34.96, 34.59, 32.19, 31.46, 30.27, 26.87, 26.59, 26.24, 24.37, 23.22, 22.89, 20.82, 18.46, 13.38.IR (CHC13): 2956 (NMe3+), 1722 (C=0, ester), 1699 (C=0, ketone), 1478 (NMe3+) 1386 (CH3), 1360(COCH3), 1230 (NMe3+), 1188 (CO), cm”1.ESI m/z 446.6 (100percent, [M-C1]+); HRMS-ESI m/z 446.3624 ([M-C1]+, C28H4803N requires 446.3629).For C28H48C1N03 (482,1) calculated: 69.75percent C; 10.03percent H, 7.35percent CI, 2.91percent N; found: 69.59percent C, 9.99percent H, 7.12 percent CI, 2.82percent N.
6249-56-5 3-Carboxy-N,N,N-trimethylpropan-1-aminium chloride 22620, acatalyst-ligand compound, is more and more widely used in various fields.
Reference£º
Patent; USTAV ORGANICKE CHEMIE A BIOCHEMIE AKADEMIE V?D ?ESKE REPUBLIKY, V.V.I.; FYZIOLOGICKY USTAV AKADEMIE V?D ?ESKE REPUBLIKY, V.V.I.; CHODOUNSKA, Hana; KAPRAS, Vojt?ch; VYKLICKY, Ladislav; BOROVSKA, Ji?ina; VYKLICKY, Vojt?ch; VALE?, Karel; STUCHLIK, Ale?; RAMBOUSEK, Luka?; WO2012/110010; (2012); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI