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【结 构 式】

【分子编号】13512

【品名】Sodium 1,2,3-thiadiazol-5-ylsulfide

【CA登记号】75849-83-1

【 分 子 式 】C2HN2NaS2

【 分 子 量 】140.165188

【元素组成】C 17.14% H 0.72% N 19.99% Na 16.4% S 45.75%

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:(XII)

The alkylation of 5-hydroxy-2-(hydroxymethyl)-4-pyrone (I) with diphenyldiazomethane in ethanol gives 5-(diphenylmethoxy)-2-(hydroxymethyl)-4-pyrone (II), which is treated with hydroxylamine in hot ethanol - water to afford 5-(diphenylmethoxy)-1-hydroxy-2-(hydroxymethyl)-4-pyridone (III). The alkylation of (III) with diphenylmethyl chloride, K2CO3 and NaI in DMSO yields 1,5-bis(diphenylmethoxy)-2-(hydroxymethyl)-4-pyridone (IV), which is condensed with N-hydroxyphthalimide (V) by means of triphenylphosphine in THF to give 1,5-bis(diphenylmethoxy)-2-(phthalimidooxymethyl)-4-pyridone (VI). The reaction of (VI) with hydrazine in ethanol affords the corresponding aminooxy derivative (VII), which is condensed with 2-[2-(triphenylmethylamino)thiazol-4-yl]glyoxylic acid (VIII) in CHCl3 - ethanol to yield 2(Z)-[1,5-bis(diphenylmethoxy)-4-oxo-1,4-dihydropyridin-2-ylmethoxyimino]-2-[2-(triphenylmethylamino)thiazol-4-yl]acetic acid (IX). The condensation of (IX) with (6R,7R)-7-amino-3-(chloromethyl)-3-cephem-4-carboxylic acid 4-methoxybenzyl ester (X) by means of NaHCO3, 1-hydroxybenzotriazole (HBT) and dicyclohexylcarbodiimide (DDC) in ethyl acetate - water gives the corresponding 7-acetamide derivative (XI), which by a new condensation with sodium 1,2,3-thiadiazole-5-thiolate (XII) in DMF - ethanol affords the fully protected final product (XIII). Finally, this compound is deprotected by a treatment with trifluoroacetic acid and anisole, the sodium salt being obtained by treatment with HaHCO3 in water.

1 Zama, Y.; Ishiyama, N.; Saita, T.; Naito, T.; Hirose, M.; Yokoyama, M.; Asano, T.; Senda, H.; Sekine, H.; Sanai, S. (Kaken Pharmaceutical Co., Ltd.); Cephalosporin cpds., processes for their preparation and antibacterial agents. EP 0251299; JP 1988146887; JP 1988152386; JP 1990288884; US 4822786; US 4883879 .
2 Prous, J.; Castaner, J.; KP-736. Drugs Fut 1990, 15, 5, 457.
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) 13501 Kojic acid; 5-Hydroxy-2-(hydroxymethyl)-4H-pyran-4-one 501-30-4 C6H6O4 详情 详情
(II) 13502 5-(Benzhydryloxy)-2-(hydroxymethyl)-4H-pyran-4-one C19H16O4 详情 详情
(III) 13503 5-(Benzhydryloxy)-1-hydroxy-2-(hydroxymethyl)-4(1H)-pyridinone C19H17NO4 详情 详情
(IV) 13504 1,5-Bis(benzhydryloxy)-2-(hydroxymethyl)-4(1H)-pyridinone C32H27NO4 详情 详情
(V) 13505 N-Hydroxyphthalimide; 2-Hydroxy-1H-isoindole-1,3(2H)-dione 524-38-9 C8H5NO3 详情 详情
(VI) 13506 2-[[1,5-Bis(benzhydryloxy)-4-oxo-1,4-dihydro-2-pyridinyl]methoxy]-1H-isoindole-1,3(2H)-dione C40H30N2O6 详情 详情
(VII) 13507 2-[(Aminooxy)methyl]-1,5-bis(benzhydryloxy)-4(1H)-pyridinone C32H28N2O4 详情 详情
(VIII) 13508 2-[2-(Benzhydrylamino)-1,3-thiazol-4-yl]-2-oxoacetic acid C18H14N2O3S 详情 详情
(IX) 13509 2-[2-(Benzhydrylamino)-1,3-thiazol-4-yl]-2-([[1,5-bis(benzhydryloxy)-4-oxo-1,4-dihydro-2-pyridinyl]methoxy]imino)acetic acid C50H40N4O6S 详情 详情
(X) 13510 4-methoxybenzyl (6R,7R)-7-amino-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C16H17ClN2O4S 详情 详情
(XI) 13511 4-methoxybenzyl (6R,7R)-7-[[2-[2-(benzhydrylamino)-1,3-thiazol-4-yl]-2-([[1,5-bis(benzhydryloxy)-4-oxo-1,4-dihydro-2-pyridinyl]methoxy]imino)acetyl]amino]-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C66H55ClN6O9S2 详情 详情
(XII) 13512 Sodium 1,2,3-thiadiazol-5-ylsulfide 75849-83-1 C2HN2NaS2 详情 详情
(XIII) 13513 4-methoxybenzyl (6R,7R)-7-[[2-[2-(benzhydrylamino)-1,3-thiazol-4-yl]-2-([[1,5-bis(benzhydryloxy)-4-oxo-1,4-dihydro-2-pyridinyl]methoxy]imino)acetyl]amino]-8-oxo-3-[(1,2,3-thiadiazol-5-ylsulfanyl)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxyl C68H56N8O9S4 详情 详情
Extended Information