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【结 构 式】

【分子编号】16479

【品名】2,3-dihydroxypropyl nicotinate

【CA登记号】

【 分 子 式 】C9H11NO4

【 分 子 量 】197.19068

【元素组成】C 54.82% H 5.62% N 7.1% O 32.45%

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:(IV)

The compound S 16961-1 was synthesized in three steps from solketal (I) by acylation with nicotinoyl chloride (II), deprotection of the isopropylidene ketal (III) by heating in dilute aqueous acetic acid and acylation of this key intermediate (IV) with a slight excess of palmitoyl chloride (V) in the presence of triethylamine and 4-dimethylaminopyridine (DMAP) as catalyst. The enantiomers of S 16961-1 were obtained independently in one step from the commercially available (d)- and (l)-1,2-dipalmitoyl glycerols by acylation with nicotinoyl chloride in the presence of triethylamine. The enantiomers were found equiactive and therefore were not pursued individually.

1 Brown, G.; Albers, J.J.; Fisher, L.D.; Schaeffer, S.; Lin, J.; Kaplan, C.; Zhao, X.; Bisson, B.; Fitzpatrick, V.; Dodge, H.; Regression of coronary artery disease as a result of intensive lipid lowering therapy in men with high level of apolipoprotein B. New Engl J Med 1990, 323, 19, 1289-98.
2 Cordi, A.A.; Duhault, J.; Laudignon, N.; Castagne, I.; S 16961-1. Drugs Fut 1996, 21, 5, 490.
3 Cordi, A.; Lacoste, J.-M.; Duhault, J.; Espinal, J.; Boulanger, M. (ADIR et Cie.); Diacylglycerol nicotinates. EP 0574312; JP 1994056786; US 5385920 .
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) 16476 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane; (2,2-dimethyl-1,3-dioxolan-4-yl)methanol; 2,3-o-Isopropylideneglycerol 100-79-8 C6H12O3 详情 详情
(II) 10753 Nicotinoyl chloride C6H4ClNO 详情 详情
(III) 16478 (2,2-dimethyl-1,3-dioxolan-4-yl)methyl nicotinate C12H15NO4 详情 详情
(IV) 16479 2,3-dihydroxypropyl nicotinate C9H11NO4 详情 详情
(V) 16480 Palmitoyl Chloride; hexadecanoyl chloride 112-67-4 C16H31ClO 详情 详情
Extended Information