(1S,5R,7R)-4-[(2S)-2-hexyl-4-pentynoyl]-10,10-dimethyl-3lambda~6~-thia-4-azatricyclo[5.2.1.0~1,5~]decane-3,3-dione -Drug Synthesis Database

【结构式】

【分子编号】58247

【品名】(1S,5R,7R)-4-[(2S)-2-hexyl-4-pentynoyl]-10,10-dimethyl-3lambda~6~-thia-4-azatricyclo[5.2.1.0~1,5~]decane-3,3-dione

【CA登记号】

【分子式】C₂₁H₃₃NO₃S

【分子量】379.56396

【元素组成】C 66.45% H 8.76% N 3.69% O 12.65% S 8.45%

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：(III)

In a related procedure, the N-octanoyl sultam (I) is alkylated by propargyl bromide (II) to produce (III). Hydrolysis of (III) by means of hydrogen peroxide-tetrabutylammonium hydroxide or lithium hydroxide-hydrogen peroxide furnishes acid (IV). Then, catalytic hydrogenation of the propargyloctanoic acid (IV) in the presence of either Pd/C or Pt/C provides the title compound.

参考文献中间体

合成目标

【1】 Hasegawa, T.; Yamamoto, H.; A practical synthesis of optically active (R)-2-propyloctanoic acid: Therapeutic agent for Alzheimer's disease. Bull Chem Soc Jpn 2000, 73, 2, 423.
【2】 Yamamoto, H. (Ono Pharmaceutical Co., Ltd.); Novel intermediates and processes for the preparation of optically active octanoic acid derivs.. EP 1078921; US 6333415; WO 9958513 .
【3】 Iguchi, Y.; Yamaguchi, K.; Toda, N. (Ono Pharmaceutical Co., Ltd.; Tokyo Kasei Kogyo Co., Ltd.); Process for the preparation of (2R)-2-propyloctanoic acid. EP 1153910; WO 0048982 .

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)	58243	(1S,5R,7R)-10,10-dimethyl-4-octanoyl-3lambda~6~-thia-4-azatricyclo[5.2.1.0~1,5~]decane-3,3-dione		C₁₈H₃₁NO₃S	详情	详情
(II)	11176	3-Bromopropyne; 3-Bromo-1-propyne	106-96-7	C₃H₃Br	详情	详情
(III)	58247	(1S,5R,7R)-4-[(2S)-2-hexyl-4-pentynoyl]-10,10-dimethyl-3lambda~6~-thia-4-azatricyclo[5.2.1.0~1,5~]decane-3,3-dione		C₂₁H₃₃NO₃S	详情	详情
(IV)	58248	(2S)-2-hexyl-4-pentynoic acid		C₁₁H₁₈O₂	详情	详情

Extended Information