848482-93-9, (S)-4-(tert-Butoxycarbonyl)piperazine-2-carboxylic acid is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,848482-93-9
To a sealed tube was added fert-butyl N-[(lS)-l -(3-bromophenyl)but-3-en-l -yl] carbamate, prepared as described in intermediate 2, (S)-benzyl (l-(3-bromophenyl)but-3-en- l-yl)carbamate (0.8 g, 2.221 mmol), (S)-4-(fer/-butoxycarbonyl)piperazine-2-carboxylic acid (0.562 g, 2.443 mmol), K2CO3 (0.921 g, 6.66 mmol) and DMSO (2.22 ml). The reaction was purged with Ar and then Cul (0.021 g, 0.111 mmol) was added. The reaction was sealed and stirred at 110 C overnight. The reaction was partitioned between water (40 ml) and EtOAc (50 ml). The organic layer was separated, washed with saturated aqueous NH4CI (40 ml), water (40 ml), and brine (40 ml). The layers were separated and the organic layer was dried over MgS04, filtered and concentrated to give crude (S)-l-(3-((S)-l- (((benzyloxy)carbonyl)amino)but-3-en-l-yl)phenyl)-4-(teri-butoxycarbonyl)piperazine-2- carboxylic acid as a greenish gum. Then to this crude material was added EtOAc (5 mL), but-3-en-l -amine (112 mg, 1.57 mmol), and pyridine (0.254 mL, 3.14 mmol) followed by addition of 2,4,6-tripropyl-l,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide (1 g, 1.570 mmol). The reaction was stirred at rt overnight. The reaction was diluted with EtOAc (30 ml) and the reaction was washed with saturated aqueous NaHC03 (20 ml), water (30 ml) and brine (30 ml). The organic layer was separated, dried over MgS04, filtered and concentrated. The residue was purified using ISCO system (0-100% EtO Ac/Hex gradient) to give (S)-tert- butyl 4-(3-((S)-l-(((benzyloxy)carbonyl)amino)but-3-en-l-yl)phenyl)-3-(but-3-en-l- ylcarbamoyl)piperazine-l-carboxylate (180 mg, 0.320 mmol, 20.4 % yield) as a white solid. (ESI) m/z: 563.4 (M+H)+. NMR (400MHz, CDCh) delta 7.36 (br. s., 4H), 7.27 – 7.23 (m, 1H), 6.85 (d, J=7.7 Hz, 1H), 6.73 (d, J=6.2 Hz, 2H), 6.65 (br. s., 1H), 5.78 – 5.54 (m, 2H), 5.21 – 5.06 (m, 5H), 5.03 – 4.92 (m, 2H), 4.76 (br. s., 1H), 4.23 – 4.10 (m, 1H), 3.99 (br. s., 1H), 3.78 – 3.64 (m, 2H), 3.55 (ddd, J=13.0, 9.7, 3.6 Hz, 1H), 3.49 – 3.42 (m, 1H), 3.41 – 3.23 (m, 3H), 2.62 – 2.44 (m, 2H), 2.24 – 2.09 (m, 2H), 1.52 – 1.48 (m, 9H).
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Reference：
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHU, Yeheng; DILGER, Andrew K.; EWING, William R.; ORWAT, Michael J.; PINTO, Donald J.P.; (156 pag.)WO2017/19821; (2017); A1;,
Piperazine – Wikipedia
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