Multi-step reaction with 11 steps
1.1: PPA / 0.08 h / 115 °C
2.1: TMEDA; NaI / acetonitrile / -5 °C
3.1: 95 percent / I2 / -5 - 20 °C
4.1: NH3 / aq. ethanol / 0 - 20 °C
4.2: L-pyroglutamic acid; 5-NO2-salicylaldehyde / propan-2-ol; H2O / 48 h / 70 °C
5.1: 99 percent / Na2CO3 / dioxane; H2O / 18 h / 20 °C
6.1: LiHMDS / tetrahydrofuran / 0 °C
6.2: tetrahydrofuran / 0 - 20 °C
7.1: 100 percent / HCl / ethyl acetate / 0 - 20 °C
8.1: 57 percent / NMM / dimethylformamide / 20 °C
9.1: 97 percent / H2 / Pd/C / methanol / 3 h / 2327.17 Torr
10.1: 83 percent / EDC; HOBt; NMM / dimethylformamide
11.1: 51 percent / NH2OH*HCl; NMM / methanol / 10 h / 20 °C
With
4-methyl-morpholine; hydrogenchloride; N,N,N,N,-tetramethylethylenediamine; hydroxylamine hydrochloride; ammonia; hydrogen; iodine; sodium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; sodium iodide; lithium hexamethyldisilazane;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
4.2: racemate resolution;
DOI:10.1016/S0960-894X(02)00010-0