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【结 构 式】 
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【药物名称】Sarpicillin, BL-P1761 【化学名称】6-(2,2-Dimethyl-5-oxo-4-phenyl-1-imidazolidinyl)penicillanic acid methoxymethyl ester 【CA登记号】40966-79-8 【 分 子 式 】C21H27N3O5S 【 分 子 量 】433.53044 |
【开发单位】Bristol-Myers Squibb (Originator) 【药理作用】Penicillins |
合成路线1
The esterification of potassium phenoxymethylpenicillanate (I) with chloromethyl methyl ether (A) in methylene chloride-THF gives the methoxymethyl ester of penicilline V (II), which is then treated with dimethylaniline (B) in CH2Cl2 to afford methoxymethyl 6-aminopenicillanate (III). Finally, this product is condensed with phenylglycyl chloride (C) hydrochloride and acetone (D) by means of NaOH.
| 【1】 Sleezer, P.D.; Johnson, D.A. (Bristol-Myers Squibb Co.); Antibacterial agents. DE 2244915; ES 406644; FR 2154488; GB 1400584; JP 48036186 . |
| 【2】 Playle, A.C.; Castaner, J.; Sarpicillin. Drugs Fut 1977, 2, 7, 478. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (B) | 17036 | N,N-dimethyl-N-phenylamine; N,N-dimethylbenzenamine; N,N-dimethylaniline | 121-69-7 | C8H11N | 详情 | 详情 |
| (A) | 18319 | Chloro(methoxy)methane; Chloromethyl methyl ether | 107-30-2 | C2H5ClO | 详情 | 详情 |
| (D) | 23199 | 2-Propanone; Acetone; beta-ketopropane; chevron acetone;propan-2-one； Dimethyl formaldehyde; Dimethyl ketone; dimethylketal; Ketone propane; Methyl ketone; Propanone; Pyroacetic acid; Pyroacetic ether | 67-64-1 | C3H6O | 详情 | 详情 |
| (I) | 40163 | potassium (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate | 132-98-9 | C16H17KN2O5S | 详情 | 详情 |
| (II) | 40164 | methoxymethyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate | C18H22N2O6S | 详情 | 详情 | |
| (III) | 40165 | methoxymethyl (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate | C10H16N2O4S | 详情 | 详情 | |
| (IV) | 40166 | methoxymethyl (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylethanoyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate | C18H23N3O5S | 详情 | 详情 | |
| (C) | 40055 | (2R)-2-amino-2-phenylethanoyl chloride | C8H8ClNO | 详情 | 详情 |