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【结 构 式】

【分子编号】37722

【品名】potassium (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[[(3R)-5-thioxopyrrolidinyl]sulfanyl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

【CA登记号】

【 分 子 式 】C14H17KN2O4S2

【 分 子 量 】380.53036

【元素组成】C 44.19% H 4.5% K 10.27% N 7.36% O 16.82% S 16.85%

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:(XV)

Oxocarbapenam (XII) was converted into vinyl phosphate (XIII) by treatment with diphenylphosphoryl chloride and diisopropylethylamine. Displacement of the phosphate group of (XIII) by 4-mercaptopyrrolidine-2-thione (IV) yielded carbapenem sulfide (XIV). After hydrogenolytic cleavage of the p-nitrobenzyl ester of (XIV) in the presence of Pd/C and KHCO3, the resulting potassium carboxylate salt (XV) was condensed with isobutyryloxymethyl iodide (XVI) to furnish the title compound.

1 Horikawa, H.; Iwasaki, T.; Kondo, K. (Tanabe Seiyaku Co., Ltd.); Process for preparing beta-lactam deriv. and synthetic intermediate thereof. EP 0559533 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV) 37712 (4R)-4-sulfanyl-2-pyrrolidinethione C4H7NS2 详情 详情
(XII) 37720 4-nitrobenzyl (4R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate C17H18N2O7 详情 详情
(XIII) 13224 4-nitrobenzyl (4R,5R,6S)-3-[(diphenoxyphosphoryl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 90776-59-3 C29H27N2O10P 详情 详情
(XIV) 37721 4-nitrobenzyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[[(3R)-5-thioxopyrrolidinyl]sulfanyl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate C21H23N3O6S2 详情 详情
(XV) 37722 potassium (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[[(3R)-5-thioxopyrrolidinyl]sulfanyl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate C14H17KN2O4S2 详情 详情
(XVI) 37723 iodomethyl 2-methylpropanoate C5H9IO2 详情 详情
(XVII) 37724 (isobutyryloxy)methyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[[(3R)-5-thioxopyrrolidinyl]sulfanyl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate C19H26N2O6S2 详情 详情
Extended Information