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【结 构 式】

【分子编号】19274

【品名】2-[4-(methylsulfonyl)phenyl]-2-oxoethyl 2-phenylacetate

【CA登记号】

【 分 子 式 】C17H16O5S

【 分 子 量 】332.37704

【元素组成】C 61.43% H 4.85% O 24.07% S 9.65%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(XXII)

7) The Friedel-Crafts condensation of thioanisole (XX) with acetyl chloride (XXI) by means of AlCl3 in dichlorobenzene gives the corresponding acetophenone (X), which is oxidized with H2O2/WO4Na2 to the ketosulfone (XI). The bromination of (XI) with Br2 in acetic acid/48% HBr affords the phenacyl bromide (XII), which is condensed with phenylacetic acid sodium salt (XXIII) in DMF, giving the phenacyl ester (XXII). Finally, this compound is cyclized by means of diisopropylamine in DMF.

1 Sorbera, L.A.; Rabasseda, X.; Castañer, J.; Rofecoxib. Drugs Fut 1998, 23, 12, 1287.
2 Frey, L.F.; Dolling, U.H.; Desmond, R.; Tillyer, R.D.; Tschaen, D.M. (Merck & Co., Inc.); Process of preparing phenyl heterocycles useful as COX-2 inhibitors. WO 9800416 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(X) 19262 1-[4-(methylsulfanyl)phenyl]-1-ethanone;4'-Methylthioacetophenon;4’-(methylthio)acetophenone 1778-09-2 C9H10OS 详情 详情
(XI) 19263 1-[4-(methylsulfonyl)phenyl]-1-ethanone; 4-methylsulfonylacetophenone 10297-73-1 C9H10O3S 详情 详情
(XII) 19264 2-bromo-1-[4-(methylsulfonyl)phenyl]-1-ethanone C9H9BrO3S 详情 详情
(XX) 19272 methyl phenyl sulfide; 1-(methylsulfanyl)benzene 100-68-5 C7H8S 详情 详情
(XXI) 19273 acetyl chloride 75-36-5 C2H3ClO 详情 详情
(XXII) 19274 2-[4-(methylsulfonyl)phenyl]-2-oxoethyl 2-phenylacetate C17H16O5S 详情 详情
(XXIII) 19275 sodium 2-phenylacetate 114-70-5 C8H7NaO2 详情 详情

合成路线2

该中间体在本合成路线中的序号:(V)

 

1 Sharma NR.Rawat GS. 2004. Synthesis of rofecoxib and study of Lactone ring stability. Asia J Chem, 16: 978~982
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) 19262 1-[4-(methylsulfanyl)phenyl]-1-ethanone;4'-Methylthioacetophenon;4’-(methylthio)acetophenone 1778-09-2 C9H10OS 详情 详情
(II) 19263 1-[4-(methylsulfonyl)phenyl]-1-ethanone; 4-methylsulfonylacetophenone 10297-73-1 C9H10O3S 详情 详情
(III) 19264 2-bromo-1-[4-(methylsulfonyl)phenyl]-1-ethanone C9H9BrO3S 详情 详情
(IV) 16148 Benzeneacetic acid; 2-Phenylacetic acid; Phenyl Acetic Acid 103-82-2 C8H8O2 详情 详情
(V) 19274 2-[4-(methylsulfonyl)phenyl]-2-oxoethyl 2-phenylacetate C17H16O5S 详情 详情
Extended Information