(1S,5R,17S)-4-(cyclopropylmethyl)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.0(1,13).0(5,17).0(7,18)]octadeca-7(18),8,10-trien-14-one -Drug Synthesis Database

【结构式】

【分子编号】42232

【品名】(1S,5R,17S)-4-(cyclopropylmethyl)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.0(1,13).0(5,17).0(7,18)]octadeca-7(18),8,10-trien-14-one

【CA登记号】

【分子式】C₂₀H₂₃NO₄

【分子量】341.40696

【元素组成】C 70.36% H 6.79% N 4.1% O 18.75%

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)

A further procedure for the preparation of (I) from naltrexone (III) has been reported. Naltrexone (III) was O-alkylated with diethyl sulfate in the presence of NaH to give (IV). Deprotonation of (IV) using the combination potassium tert-butoxide/butyllithium, followed by methylation with dimethyl sulfate, yielded the 5-methyl derivative (V). The aryl- and enol ether groups of (V) were then cleaved by means of concentrated HBr.

参考文献中间体

合成目标

【1】 Krassing, R.; et al.; A novel method for the introduction of a 5-beta-methyl group into 4,5-alpha-epoxymorphinan-6-ones via the enol ether. Helv Chim Acta 2000, 83, 2, 380.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	42229	(1R,5R,13R,17S)-4-(cyclopropylmethyl)-17-ethoxy-10-hydroxy-13-methyl-12-oxa-4-azapentacyclo[9.6.1.0(1,13).0(5,17).0(7,18)]octadeca-7(18),8,10-trien-14-one	C₂₃H₂₉NO₄	详情	详情
(III)	42232	(1S,5R,17S)-4-(cyclopropylmethyl)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.0(1,13).0(5,17).0(7,18)]octadeca-7(18),8,10-trien-14-one	C₂₀H₂₃NO₄	详情	详情
(IV)	42230	(1S,5R,17S)-4-(cyclopropylmethyl)-10,14,17-triethoxy-12-oxa-4-azapentacyclo[9.6.1.0(1,13).0(5,17).0(7,18)]octadeca-7(18),8,10,14-tetraene; (1S,5R)-4-(cyclopropylmethyl)-10,14-diethoxy-12-oxa-4-azapentacyclo[9.6.1.0(1,13).0(5,17).0(7,18)]octadeca-7(18),8,10,14-tetraen-17-yl ethyl ether	C₂₆H₃₅NO₄	详情	详情
(V)	42231	(1R,5R,13R,17S)-4-(cyclopropylmethyl)-10,14,17-triethoxy-13-methyl-12-oxa-4-azapentacyclo[9.6.1.0(1,13).0(5,17).0(7,18)]octadeca-7(18),8,10,14-tetraene; (1R,5R,13R)-4-(cyclopropylmethyl)-10,14-diethoxy-13-methyl-12-oxa-4-azapentacyclo[9.6.1.0(1,13).0(5,17).0(7,18)]octadeca-7(18),8,10,14-tetraen-17-yl ethyl ether	C₂₇H₃₇NO₄	详情	详情

Extended Information