With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.167316-27-0,N-((1S,2S)-2-Amino-1,2-diphenylethyl)-4-methylbenzenesulfonamide,as a common compound, the synthetic route is as follows.
Step 2 Scheme:- S, ? //–/N/ TEAF, I—) N 0 N 0 0 Compound 2 Compound 3 S-TsDPENMaterials : – Material Wt (g) MW Moles Equivs Compound 2 9 402. 79 0. 0224 1 DMF 39.5 73.09 0.54 24.16 (Rh Cp*C12) 2 0.0691 618.0 1. 12 x 104 5. 0 x 10-3 S, S-Ts DPEN 0.0817 366.0 2. 23 x 104 10. 0 x 10-3 DMF 7.5 73.09 0.103 4.59 TEAF 4. 65–2. 50 Cp* = pentamethylcyclopentadiene A 250 ML jacketed reactor set up with overhead stirrer, condenser, thermocouple and sparge pipe situated below the level of the agitator was assembled. The purified Compound 2 (9g) was charged to the reactor with DMF (39.5g). Freshly made catalyst (Rh CP*CI2) 2 (69.1 mg) and ligand S, S-Ts DPEN (N-p-toluenesulphonyl-1, 2- diphenylethylene-1, 2-diamine, 817 mg) in DMF (7.5g) was then charged. The contents were cooled to 10C and a nitrogen sparge rate of 1.2 L/min was established. The agitation was on full at 400 RPM. A solution of TEAF (triethylamine : formic acid mixture in 2: 5 mole ratio, 4.65 mis) was added drop-wise over 11.5 hrs overnight. The reaction was quenched with water (50MIS), a 15C exotherm (10-25C) was observed upon addition of the first 20 mis. The remaining 30 mis was added at <20C (bath temperature: 0C). Toluene was then charged (60 mis) at 20C. The reaction mass was agitated and allowed to settle respectively for 30 minutes each. The sparge was switched off at this point. The bottom red aqueous phase was back extracted with toluene (3X50M1S). The three resulting toluene phases were combined with the first black/brown organic phase. The combined reaction mass was concentrated down to a residual mass of 14.18g. The material obtained was then subjected to 3 repeats of the reduction and work up procedure, using freshly prepared catalyst for each repeat, to achieve 87% conversion, and a product mass of 7.8 g., 167316-27-0
167316-27-0 N-((1S,2S)-2-Amino-1,2-diphenylethyl)-4-methylbenzenesulfonamide 6612782, acatalyst-ligand compound, is more and more widely used in various fields.
Reference£º
Patent; AVECIA LIMITED; WO2005/28437; (2005); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI