L-750034

2(S)-(苯磺酰氨基)-3-[4-(1-哌嗪基)苯甲酰氨基]丙酸Chemical Name: 2(S)-(Phenylsulfonamido)-3-[4-(1-piperazinyl)benzamido]propionic acid
CAS No. 163209-37-8
项目整合开发状态: Preclinical
项目研究机构: Merck & Co. (Originator)
合成路线:The condensation of L-asparagine (I) with benzenesulfonyl chloride (II) in the presence of NaOH gave sulfonamide (III).Subsequent Hofmann rearrangement of (III) employing sodium hypobromite produced the diaminopropionic acid derivative (IV),which was protected as the tert-butyl ester (V) using isobutylene in the presence of H2SO4.Condensation of methyl 4-aminobenzoate (VI) with bis(2-chloroethyl)amine (VII) in refluxing butanol yielded the arylpiperazine (VIII),which was protected with di tert-butyl dicarbonate to give the corresponding carbamate (IX).Basic hydrolysis of the methyl ester of (IX) provided carboxylic acid (X).This was then coupled with amine (V) using benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP) to afford amide (XI).Finally,deprotection of the tert-butyl ester and BOC group of (XI) with trifluoroacetic acid furnished the title compound.