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【结 构 式】

【分子编号】59555

【品名】trimethylsilyl (2S)-2-amino-3-{4-[(trimethylsilyl)oxy]phenyl}propanoate

【CA登记号】

【 分 子 式 】C15H27NO3Si2

【 分 子 量 】325.55532

【元素组成】C 55.34% H 8.36% N 4.3% O 14.74% Si 17.25%

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:(XXVIII)

In a variation of this process, L-tyrosine (XXVII) was initially protected as the bis-O-silylated derivative (XXVIII) employing N,O-bis(trimethylsilyl) trifluoroacetamide. Acylation of (XXVIII) with butanesulfonyl chloride (XIV), followed by hydrolysis of the silyl groups, gave rise to N-butanesulfonyl tyrosine (XXIX). The phenolic hydroxyl of (XXIX) was then alkylated by 4-(4-pyridinyl)butyl chloride (XXII) to produce ether (XXVI). Finally, hydrogenation of the pyridine ring furnished the target piperidine derivative, which was isolated as the corresponding hydrochloride salt.

1 Chung, J.Y.L.; Zhao, D.; Hughes, D.L. (Merck & Co., Inc.); Process for preparing fibrinogen receptor antagonists. WO 9316995 .
2 Chung, J.Y.L.; Zhao, D.; Hughes, D.L.; Grabowski, E.E.; A practical synthesis of fibrinogen receptor antagonist MK-383 - Selective functionalization of (S)-tyrosine. Tetrahedron 1993, 49, 26, 5767.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XIV) 26779 1-butanesulfonyl chloride 2386-60-9 C4H9ClO2S 详情 详情
(XXII) 59551 4-(4-chlorobutyl)pyridine C9H12ClN 详情 详情
(XXVI) 59554 (2S)-2-[(butylsulfonyl)amino]-3-{4-[4-(4-pyridinyl)butoxy]phenyl}propanoic acid C22H30N2O5S 详情 详情
(XXVII) 48794 (S)-(-)-Tyrosine; (S)-2-Amino-3-(4-hydroxyphenyl)propionic acid; 3-(4-Hydroxyphenyl)-L-alanine; L-(-)-Tyrosine; L-3-(4-Hydroxyphenyl)alanine; L-4-Hydroxy-17O-phenylalanine; L-beta-(p-Hydroxyphenyl)alanine; L-Hydroxy Phenyl Alanine; L-tyrosine 60-18-4 C9H11NO3 详情 详情
(XXVIII) 59555 trimethylsilyl (2S)-2-amino-3-{4-[(trimethylsilyl)oxy]phenyl}propanoate C15H27NO3Si2 详情 详情
(XXIX) 59556 (2S)-2-[(butylsulfonyl)amino]-3-(4-hydroxyphenyl)propanoic acid C13H19NO5S 详情 详情
Extended Information