• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】25966

【品名】1'-(Tert-butoxycarbonyl)-4,4'-bipiperidine-1-carbothioamide

【CA登记号】

【 分 子 式 】C16H29N3O2S

【 分 子 量 】327.49128

【元素组成】C 58.68% H 8.93% N 12.83% O 9.77% S 9.79%

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:(V)

The selective monoprotection of 4-(4-piperidyl)piperidine (I) gives the carbamate (II), which is condensed with the isothiocyante (III) in chloroform to yield the N-(ethoxycarbonyl)carbothioamide (IV). Decarboxylation of (IV) by means of NaOH in ethanol affords the free thioamide (V), which is cyclized with 2-chloro-4-methyl-3-oxopentanoic acid ethyl ester (VI) by means of triethylamine in ethanol to provide the thiazole derivative (VII). Hydrolysis of theester group of (VII) with NaOH in ethanol gives the carboxylic acid (VIII), which is condensed with 3-amino-2(S)-(phenylsulfonamido)propionic acid methyl ester (IX), by means of DCC, HOBT and triethylamine in DMF yielding the protected target compound (X). Finally, this compound is hydrolyzed and deprotected by a treatment with HCl in ethanol. The intermediate 3-amino-2(S)-(phenylsulfonamido)propionic acid methyl ester (IX) has been obtained as follows: The reaction of L-asparagine (XI) with benzenesulfonyl chloride (XII) by means of NaOH in dioxane/water gives the sulfonated asparagine (XIII), which is submitted to Hofmann degradation with Br2 and NaOH in water and finally esterified with SOCl2 and methanol.

1 Forn, J.; Merlos, M.; Garcia-Rafanell, J.; Carceller, E.; Gomez, L.A.; Novel N-(thiazolyl-5-carbonyl)-beta-alanine derivatives as potent, orally active fibrinogen receptor antagonists. 216th ACS Natl Meet (Aug. 23-27, Boston) 1998, Abst MEDI 079.
2 Carceller, E.; Jimenez, P.J.; Salas, J. (J. Uriach & Cia., SA); Novel carboxamides as platelet aggregation inhibitors. WO 9846599 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 25962 4,4'-bipiperidine C10H20N2 详情 详情
(II) 25963 4,4'-bipiperidine-1-carboxylic acid tert-butyl ester C15H28N2O2 详情 详情
(III) 25964 1-[(isothiocyanatocarbonyl)oxy]ethane 16182-04-0 C4H5NO2S 详情 详情
(IV) 25965 N-[1'-(Tert-butoxycarbonyl)-4,4'-bipiperidin-1-yl-thiocarbonyl]carbamic acid ethyl ester C19H33N3O4S 详情 详情
(V) 25966 1'-(Tert-butoxycarbonyl)-4,4'-bipiperidine-1-carbothioamide C16H29N3O2S 详情 详情
(VI) 25967 ethyl 2-chloro-4-methyl-3-oxopentanoate C8H13ClO3 详情 详情
(VII) 25968 2-[1'-(Tert-butoxycarbonyl)-4,4'-bipiperidin-1-yl]-4-isopropylthiazole-5-carboxylic acid ethyl ester C24H39N3O4S 详情 详情
(VIII) 25969 2-[1'-(Tert-butoxycarbonyl)-4,4'-bipiperidin-1-yl]-4-isopropylthiazole-5-carboxylic acid C22H35N3O4S 详情 详情
(IX) 25970 methyl (2S)-3-amino-2-[(phenylsulfonyl)amino]propanoate C10H14N2O4S 详情 详情
(X) 25971 (2(S)-(Benzenesulfonamido)-3-[2-[4-[1-tert-butoxycarbonyl)piperidin-4-yl]piperidin-4-yl]-4-isopropylthiazol-5-ylcarboxamido]propionic acid methyl ester; (2(S)-(Benzenesulfonamido)-3-[2-[4-[1-tert-butoxycarbonyl)piperidin-4-yl]piperidin-4-yl]-4-isopropylthiazol-5-ylcarboxamido]propionic acid methyl ester C32H47N5O7S2 详情 详情
(XI) 25972 S-(+)-Asparagine; S-(+)-2-Aminosuccinamic acid; L-Asparagine 70-47-3 C4H8N2O3 详情 详情
(XII) 14713 benzenesulfonyl chloride 98-09-9 C6H5ClO2S 详情 详情
(XIII) 25973 (2S)-4-amino-4-oxo-2-[(phenylsulfonyl)amino]butyric acid C10H12N2O5S 详情 详情
Extended Information