(2S)-2-piperidinecarboxylic acid -Drug Synthesis Database

【结构式】

【分子编号】45303

【品名】(2S)-2-piperidinecarboxylic acid

【CA登记号】

【分子式】C₆H₁₁NO₂

【分子量】129.15888

【元素组成】C 55.8% H 8.58% N 10.84% O 24.77%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(II)

The compound has been obtained biosynthetically by an optimized fermentation process using Streptomyces hygroscopicus mutant RSH 1701 with a complex culture medium were [14C]-labeled (1R,3R,4R)-2,3-dichydroxycyclo-hexanecarboxylic acid (I) and [14C]-labeled (S)-pipecolic acid (II) have been added. This fermentation process yielded [14C]-labeled rapamycin (III), which was finally selectively O-alkylated at the C-40 position with monosilylated ethylene glycol triflate in DMSO/dimethoxyethane.

参考文献中间体

合成目标

【1】 Moenius, T.; et al.; C-14 labelling of NVP RAD001 - A new rapamycin derivative. J Label Compd Radiopharm 1999, 42, 1, 29.

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)	32019	(1R,3R,4R)-3,4-dihydroxycyclohexanecarboxylic acid		C₇H₁₂O₄	详情	详情
(I)	45302	(1R,3R,4R)-3,4-dihydroxycyclohexanecarboxylic acid		C₇H₁₂O₄	详情	详情
(II)	17380	(2S)hexahydro-2-pyridinecarboxylic acid; (S)-pipecolic acid	3105-95-1	C₆H₁₁NO₂	详情	详情
(II)	45303	(2S)-2-piperidinecarboxylic acid		C₆H₁₁NO₂	详情	详情
(III)	20296	(1R,9S,12S,15R,18R,19R,21R,23S,30S,32S,35R)-1,18-dihydroxy-12-[(1R)-2-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethyl]-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.0(4,9)]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone	53123-88-9	C₅₁H₇₉NO₁₃	详情	详情
(III)	45304	(1R,9S,12S,15R,18R,19R,21R,23S,30S,32S,35R)-1,18-dihydroxy-12-[(1R)-2-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethyl]-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.0(4,9)]hexatriaconta-16,24,26,28-tetraene-2		C₅₁H₇₉NO₁₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

The reaction of the labeled acylated (-)-bornane-10,2-sultam (XI) with benzophenone imine (XII) gives the glycylsultam derivative (XIII), which is alkylated with 4-iodobutyl chloride (XIV) by means of butyllithium and DMPU in THF yielding intermediate (XV). The selective hydrolysis of (XV) with HCl affords the omega-chloro-L-norleucine derivative (XVI), which is cyclized by means of tetrabutylammonium fluoride and DIEA in hot acetonitrile giving the (2S)-piperidyl derivative (XVII). Finally, this compound is hydrolyzed with LiOH in THF/water to the labeled intermediate (II).

参考文献中间体

合成目标

【1】 Moenius, T.; et al.; C-14 labelling of NVP RAD001 - A new rapamycin derivative. J Label Compd Radiopharm 1999, 42, 1, 29.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(II)	17380	(2S)hexahydro-2-pyridinecarboxylic acid; (S)-pipecolic acid	3105-95-1	C₆H₁₁NO₂	详情	详情
(II)	45303	(2S)-2-piperidinecarboxylic acid		C₆H₁₁NO₂	详情	详情
(XI)	32030	(1R,5R)-4-(2-bromoacetyl)-10,10-dimethyl-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decane-3,3-dione		C₁₂H₁₈BrNO₃S	详情	详情
(XI)	45315	(1R,5R)-4-(2-bromoacetyl)-10,10-dimethyl-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decane-3,3-dione		C₁₂H₁₈BrNO₃S	详情	详情
(XII)	32024	diphenylmethanimine	1013-88-3	C₁₃H₁₁N	详情	详情
(XIII)	32025	(1R,5R)-4-[2-[(dibenzylene)amino]acetyl]-10,10-dimethyl-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decane-3,3-dione		C₂₅H₂₈N₂O₃S	详情	详情
(XIII)	45311	(1R,5R)-4-[2-[(dibenzylene)amino]acetyl]-10,10-dimethyl-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decane-3,3-dione		C₂₅H₂₈N₂O₃S	详情	详情
(XIV)	32026	1-chloro-4-iodobutane	10297-05-9	C₄H₈ClI	详情	详情
(XV)	32027	(1R,5R)-4-[(2S)-6-chloro-2-[(dibenzylene)amino]hexanoyl]-10,10-dimethyl-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decane-3,3-dione		C₂₉H₃₅ClN₂O₃S	详情	详情
(XV)	45312	(1R,5R)-4-[(2S)-6-chloro-2-[(dibenzylene)amino]hexanoyl]-10,10-dimethyl-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decane-3,3-dione		C₂₉H₃₅ClN₂O₃S	详情	详情
(XVI)	32028	(1R,5R)-4-[(2S)-2-amino-6-chlorohexanoyl]-10,10-dimethyl-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decane-3,3-dione		C₁₆H₂₇ClN₂O₃S	详情	详情
(XVI)	45313	(1R,5R)-4-[(2S)-2-amino-6-chlorohexanoyl]-10,10-dimethyl-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decane-3,3-dione		C₁₆H₂₇ClN₂O₃S	详情	详情
(XVII)	32029	(1R,5R)-10,10-dimethyl-4-[(2S)piperidinylcarbonyl]-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decane-3,3-dione		C₁₆H₂₆N₂O₃S	详情	详情
(XVII)	45314	(1R,5R)-10,10-dimethyl-4-[(2S)piperidinylcarbonyl]-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decane-3,3-dione		C₁₆H₂₆N₂O₃S	详情	详情

Extended Information