144164-11-4, Thiazol-5-ylmethyl ((2S,3S,5S)-5-amino-3-hydroxy-1,6-diphenylhexan-2-yl)carbamate is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
Thiazol-5-ylmethyl ((2S,3S,5S)-5-((S)-2-amino-3-methylbutanamido)-3-hydroxy-l ,6- diphenylhexan-2-yl)carbamate, compound C2: 526 mg (1.64 mmol, 1.0 eq) of TBTU was added to 356 mg (1.64 mmol, 1.0 eq) Boc-Val dissolved in 1.5 ml of DMF along with 690 mu of DIEA (3.94 mmol, 2.4 eq). The crude hydrolysate of RTV (700 mg, 1.64 mmol, 1.0 eq), dissolved in 1 ml of DMF, was added after 5 minutes of stirring in one portion. The reaction was left overnight and DMF was rotary evaporated. The reaction mixture was dissolved in 50 ml of EtOAc and washed two times by saturated NaHC03, two times with 10 % KHS04 and once with brine. The organic mixture was dried, evaporated and the product was purified using Flash chromatography (TLC analysis: EtOAc, R/ = 0.65). Product was further dissolved in 5 ml of hot EtOAc and 5 ml of diethyl ether was added. The resulting gel was filtrated and dried to give very pure (>99 %, HPLC) 250 mg of product (yield = 25 %). The product was then treated with TFA (approx. 1 ml) for 15 minutes, alternately sonicated and stirred. The remaining TFA was then removed by flow of nitrogen. The oily product was dissolved in water/ ACN and was lyophilisated. Analytical HPLC Rr = 17.4 min. HRMS (ESI+): calculated for C28H37O4N4S [M]+ 525.25300. Found 525.25292. NMR (500 MHz, DMSO-d6): 9.06 (d, 1H, 4/ = 0.8, N-CH-S), 8.24 (d, 1H / = 8.2, -NH-CO), 8.00 (bd, 3H, / = 5.2, -NH3+), 7.85 (q, 1H, 4J = 0.8, S-C-CH-N), 7.28-7.13 (m, 10H, Ph-), 6.94 (d, / = 9.4, 1H, NH-CO-O), 5.12 (d, 2H, 4J = 0.8, 0-CH2), 4.16 (m, 1H, CH-NH- CO), 3.78 (m, 1H, CH-NH3+, partial overlap with water residual peak), 3.58 (td, 1H, / = 6.8, / = 2.0, CH-OH), 3.48 (m, 1H, Ph-CH2-CH-NH), 2.72-2.67 (m, 4H, 2xCH-CH2-Ph), 2.00 (m, 1H, CH-(CH3)2), 1.50 (m, 1H, OH-CH-CH2), 1.43 (m, 1H, OH-CH-CH2), 0.89 (d, 3H, / = 6.8 -CH3), 0.84 (d, 3H, / = 6.8 -CH3). 13C NMR (125.7 MHz, DMSO-d6): 167.33 (CO Val), 158.33(q, /CF = 34.4, CF3COO-), 155.79 (O-C-N), 155.71 (N-CH-S), 143.23 (S-C-CH-N), 139.50 (Ph), 138.55 (Ph), 134.23 (S-C-CH-N), 129.56 (Ph), 129.17 (Ph), 128.30 (Ph), 128.25 (Ph), 126.26 (Ph), 126.09 (Ph), 116.44 (q, JQF = 294.8, CF3-COO ) 68.90 (HO-CH), 57.56 (CO-CH-NH3), 57.44 (COO-CH2), 55.74 (HO-CH-CH-NH), 47.98 (CONH-CH), 39.75 (NH-CH-CH2-Ph), 37.77 (-CH2-CH-CH-), 37.33 (Ph-CH2-CH-NH), 30.04 (CH(CH3)2), 17.26 and 18.69 (2xCH3).
144164-11-4 Thiazol-5-ylmethyl ((2S,3S,5S)-5-amino-3-hydroxy-1,6-diphenylhexan-2-yl)carbamate 11101978, athiazole compound, is more and more widely used in various.
Reference£º
Patent; USTAV ORGANICKE CHEMIE A BIOCHEMIE AV CR, V.V.I.; USTAV MAKROMOLEKULARNI CHEMIE AV CR, V.V.I.; UNIVERZITA KARLOVA V PRAZE, PRIRODOVEDECKA FAKULTA; SACHA, Pavel; KONVALINKA, Jan; SCHIMER, Jiri; KNEDLIK, Tomas; NAVRATIL, Vaclav; TYKVART, Jan; SEDLAK, Frantisek; MAJER, Pavel; CIGLER, Petr; SUBR, Vladimir; ULBRICH, Karel; STROHALM, Jiri; (53 pag.)WO2016/112883; (2016); A2;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica