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【结 构 式】

【分子编号】34553

【品名】(2S)-3,3,3-trifluoro-2-methyl-2-[(trimethylsilyl)oxy]propanoyl chloride

【CA登记号】

【 分 子 式 】C7H12ClF3O2Si

【 分 子 量 】248.7044896

【元素组成】C 33.81% H 4.86% Cl 14.25% F 22.92% O 12.87% Si 11.29%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VI)

Alkylation of an equimolecular mixture of trans-2,5-dimethylpiperazine dihydrochloride (I) and the free base (II) with benzyl chloride produced the racemic monobenzyl piperazine, which was resolved using (-)-tartaric acid to yield the required (2R,5S)-isomer (III). (R)-3,3,3-Trifluoro-2-hydroxy-2-methylpropionic acid (IV) was protected as the silyl derivative (V) using bis(trimethylsilyl)urea, and subsequently converted to acid chloride (VI) by means of oxalyl chloride. Coupling of acid chloride (VI) with the chiral piperazine (III) afforded amide (VII), which was desilylated in methanolic HCl yielding (VIII). Hydrogenolysis of the N-benzyl group of (VIII) over Pd/C gave piperazine (IX). Finally, coupling of (IX) with 4-cyanobenzoyl chloride (X) furnished the corresponding bisamide.

1 Anderson, R.C.; Aicher, T.D.; Bebernitz, G.R.; et al.; (R)-3,3,3-trifluoro-2-hydroxy-2-methyl-propionamides are orally active inhibitors of pyruvate dehydrogenase kinase. J Med Chem 1999, 42, 15, 2741.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
19171 1-(Chloromethyl)benzene; Benzyl chloride 100-44-7 C7H7Cl 详情 详情
(I),(II) 20687 (2R,5S)-2,5-dimethylpiperazine C6H14N2 详情 详情
(III) 34550 (2R,5S)-1-benzyl-2,5-dimethylpiperazine C13H20N2 详情 详情
(IV) 34551 (2R)-3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid 114715-77-4 C4H5F3O3 详情 详情
(V) 34552 trimethylsilyl (2R)-3,3,3-trifluoro-2-methyl-2-[(trimethylsilyl)oxy]propanoate C10H21F3O3Si2 详情 详情
(VI) 34553 (2S)-3,3,3-trifluoro-2-methyl-2-[(trimethylsilyl)oxy]propanoyl chloride C7H12ClF3O2Si 详情 详情
(VII) 34554 (2R)-1-[(2S,5R)-4-benzyl-2,5-dimethylpiperazinyl]-3,3,3-trifluoro-2-methyl-2-[(trimethylsilyl)oxy]-1-propanone C20H31F3N2O2Si 详情 详情
(VIII) 34555 (2R)-1-[(2S,5R)-4-benzyl-2,5-dimethylpiperazinyl]-3,3,3-trifluoro-2-hydroxy-2-methyl-1-propanone C17H23F3N2O2 详情 详情
(IX) 34556 (2R)-1-[(2S,5R)-2,5-dimethylpiperazinyl]-3,3,3-trifluoro-2-hydroxy-2-methyl-1-propanone C10H17F3N2O2 详情 详情
(X) 19280 4-cyanobenzoyl chloride 6068-72-0 C8H4ClNO 详情 详情
Extended Information