|
【结 构 式】 
|
【分子编号】15898 【品名】1H-1,2,3-triazole-4-thiol; 1H-1,2,3-triazol-4-ylhydrosulfide 【CA登记号】 |
【 分 子 式 】C2H3N3S 【 分 子 量 】101.13204 【元素组成】C 23.75% H 2.99% N 41.55% S 31.71% |
合成路线1
该中间体在本合成路线中的序号：(X)2) The condensation of 1,2,3-triazol-4-thiol (X) with bromochloromethane by means of NaH gives 4-(chloromethylsulfanyl)-1,2,3-triazole (XI) with is treated with NaI in hot acetone to afford 4-(iodomethylsulfanyl)-1,2,3-triazole (XII). The reaction of (XII) with the silver mercaptide of the 7beta-[2-[2-(tert-butoxycarbonylamino)thiazol-4-yl]-2(Z)-(triphenylmethoxyimino)acetamido]-3-sulfanyl-3-cephem-4-carboxylic acid diphenylmethyl ester 1beta-oxide (XIII) in HMPT yields the condensation product (XV), which is then treated with PCl3 in DMF to eliminate the 1beta-oxide oxygen, affording the protected compound (XVI), which is deprotected with AlCl3 in anisole, as before.
| 【1】 Mealy, N.; Castaner, J.; S-1090. Drugs Fut 1996, 21, 3, 254. |
| 【2】 Kubota, T.; Kume, M. (Shionogi & Co. Ltd.); Thioalkylthio cephalosporin derivs. EP 0467647; JP 1992234346; JP 1993059066; US 5214037 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 19740 | bromo(chloro)methane | 74-97-5 | CH2BrCl | 详情 | 详情 | |
| (X) | 15898 | 1H-1,2,3-triazole-4-thiol; 1H-1,2,3-triazol-4-ylhydrosulfide | C2H3N3S | 详情 | 详情 | |
| (XI) | 15899 | 4-[(chloromethyl)sulfanyl]-1H-1,2,3-triazole; chloromethyl 1H-1,2,3-triazol-4-yl sulfide | C3H4ClN3S | 详情 | 详情 | |
| (XII) | 15900 | iodomethyl 1H-1,2,3-triazol-4-yl sulfide; 4-[(iodomethyl)sulfanyl]-1H-1,2,3-triazole | C3H4IN3S | 详情 | 详情 | |
| (XIII) | 15901 | 7beta-[2-[2-(tert-butoxycarbonylamino)thiazol-4-yl]-2(Z) -(triphenylmethoxyimino)acetamido]-3-sulfanyl-3-cephem-4-carboxylic acid dibenzyl ester 1beta-oxide; (6R,7R)-7-[2-[2-(Tert-butoxycarbonylamino)thiazol-4-yl]-2-(triphenylmethoxyimino)acetamido]-3-sulfanyl-3-cephem-4-carboxylic acid dibenzyl ester 1-oxide silver salt | C49H42AgN5O8S3 | 详情 | 详情 | |
| (XIV) | 15902 | benzhydryl (6R,7R)-7-([2-[2-[(tert-butoxycarbonyl)amino]-1,3-thiazol-4-yl]-2-[(trityloxy)imino]acetyl]amino)-5,8-dioxo-3-sulfanyl-5lambda(4)-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C49H43N5O8S3 | 详情 | 详情 | |
| (XV) | 15903 | benzhydryl (6R,7R)-7-([2-[2-[(tert-butoxycarbonyl)amino]-1,3-thiazol-4-yl]-2-[(trityloxy)imino]acetyl]amino)-5,8-dioxo-3-[[(1H-1,2,3-triazol-4-ylsulfanyl)methyl]sulfanyl]-5lambda(4)-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C52H46N8O8S4 | 详情 | 详情 | |
| (XVI) | 15904 | benzhydryl (6R,7R)-7-([2-[2-[(tert-butoxycarbonyl)amino]-1,3-thiazol-4-yl]-2-[(trityloxy)imino]acetyl]amino)-8-oxo-3-[[(1H-1,2,3-triazol-4-ylsulfanyl)methyl]sulfanyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C52H46N8O7S4 | 详情 | 详情 |