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【结 构 式】

【分子编号】42203

【品名】allyl (2S,4S)-4-(acetylsulfanyl)-2-(hydroxymethyl)-1-pyrrolidinecarboxylate

【CA登记号】

【 分 子 式 】C11H17NO4S

【 分 子 量 】259.32632

【元素组成】C 50.95% H 6.61% N 5.4% O 24.68% S 12.37%

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:(VI)

trans-4-Hydroxy-L-proline (I) was esterified with methanolic HCl, generated from acetyl chloride in MeOH, and the resulting 4-hydroxyproline methyl ester (II) was protected with allyl chloroformate to afford the allyl carbamate (III). Mesylation of the hydroxyl group of (III) with methanesulfonyl chloride, followed by reduction of the methyl ester with LiBH4, provided the alcohol (V). The mesylate group of (V) was then displaced by potassium thioacetate yielding thioacetate ester (VI). Iodo compound (VII) was obtained by mesylation of alcohol (VI) followed by substitution with NaI in acetone. 1-Methyl-5-mercaptotetrazole (IX), prepared by reaction of methyl isothiocyanate (VIII) with NaN3, was then condensed with iodide (VII) to give adduct (X). After deacetylation of thioacetate (X) with methanolic NaOH, the resulting pyrrolidinethiol (XI) was coupled with enol phosphate (XII) to give the protected carbapenem (XIII). The allyl ester and carbamate protecting groups of (XIII) were finally removed by treatment with Bu3SnH in the presence of palladium catalyst.

1 Kim, D.J.; Koo, K.D.; Shin, K.J.; Kim, C.; Park, S.W.; Yoo, K.H.; Synthesis and biological properties of new 1beta-methylcarbapenems having tetrazolothioether moiety. Bioorg Med Chem Lett 2000, 10, 13, 1421.
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) 14489 (2S,4R)-4-hydroxytetrahydro-1H-pyrrole-2-carboxylic acid; L-Hydroxyproline 51-35-4 C5H9NO3 详情 详情
(II) 15796 methyl (2S,4R)-4-hydroxytetrahydro-1H-pyrrole-2-carboxylate C6H11NO3 详情 详情
(III) 42200 1-allyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate C10H15NO5 详情 详情
(IV) 42201 1-allyl 2-methyl (2S,4R)-4-[(methylsulfonyl)oxy]-1,2-pyrrolidinedicarboxylate C11H17NO7S 详情 详情
(V) 42202 allyl (2S,4R)-2-(hydroxymethyl)-4-[(methylsulfonyl)oxy]-1-pyrrolidinecarboxylate C10H17NO6S 详情 详情
(VI) 42203 allyl (2S,4S)-4-(acetylsulfanyl)-2-(hydroxymethyl)-1-pyrrolidinecarboxylate C11H17NO4S 详情 详情
(VII) 42204 allyl (2S,4S)-4-(acetylsulfanyl)-2-(iodomethyl)-1-pyrrolidinecarboxylate C11H16INO3S 详情 详情
(VIII) 12092 Methyl isothiocyanate; MITC; (Methylimino)(thioxo)methane 556-61-6 C2H3NS 详情 详情
(IX) 28420 5-Mercapto-1-methyl-1H-tetrazole; 1-Methyl-1H-1,2,3,4-tetraazol-5-ylhydrosulfide 13183-79-4 C2H4N4S 详情 详情
(X) 42205 allyl (2S,4S)-4-(acetylsulfanyl)-2-[[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]methyl]-1-pyrrolidinecarboxylate C13H19N5O3S2 详情 详情
(XI) 42206 allyl (2S,4S)-2-[[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]methyl]-4-sulfanyl-1-pyrrolidinecarboxylate C11H17N5O2S2 详情 详情
(XII) 32617 allyl (4R,5R,6S)-3-[(diphenoxyphosphoryl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate C25H26NO8P 详情 详情
(XIII) 42207 allyl (4R,5S,6S)-3-[((3S,5S)-1-[(allyloxy)carbonyl]-5-[[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]methyl]pyrrolidinyl)sulfanyl]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate C24H32N6O6S2 详情 详情
Extended Information