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【结 构 式】 
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【分子编号】22670 【品名】benzyl (E)-3-(5-oxo-2-pyrrolidinyl)-2-propenoate 【CA登记号】 |
【 分 子 式 】C14H15NO3 【 分 子 量 】245.27804 【元素组成】C 68.56% H 6.16% N 5.71% O 19.57% |
合成路线1
该中间体在本合成路线中的序号：(VIII)The esterification of bromoacetic acid (I) with benzyl alcohol (II) gives the corresponding ester (III), which by reaction with triphenylphosphine (IV) in hot toluene yields the phosphonium bromide (V). The reaction of (V) with NaOH in water-dichloromethane affords benzyl(triphenylphosphoranylidene) acetate (VI), which is submitted to a Wittig condensation with 5-(hydroxymethyl)-2-pyrrolidone (VII) in the presence of Dess-Martin periodinane (DMPI) giving benzyl 3-(5-oxo-2-pyrrolidinyl)-2(E) propenoate (VIII). The acylation of (VIII) with 4-methoxybenzoyl chloride (IX) by means of triethylamine in hot toluene yields the corresponding amide (X), which is finally hydrogenated and deprotected with H2 over Pd/C in THF.
| 【1】 Huang, C.C.; Synthesis of carbon-14 labeled 1-(4-methoxybenzoyl. J Label Compd Radiopharm 1987, 24, 6, 675. |
| 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) | 23660 | 2-Bromoacetic acid | 79-08-3 | C2H3BrO2 | 详情 | 详情 |
| (II) | 18710 | Benzyl alcohol; Phenylmethanol | 100-51-6 | C7H8O | 详情 | 详情 |
| (III) | 12869 | benzyl 2-bromoacetate | 5437-45-6 | C9H9BrO2 | 详情 | 详情 |
| (IV) | 12437 | Triphenylphosphine; Triphenyl phosphine | 603-35-0 | C18H15P | 详情 | 详情 |
| (V) | 22667 | [2-(benzyloxy)-2-oxoethyl](triphenyl)phosphonium bromide | C27H24BrO2P | 详情 | 详情 | |
| (VI) | 22668 | benzyl 2-(triphenylphosphoranylidene)acetate | C27H23O2P | 详情 | 详情 | |
| (VII) | 10079 | 5-(Hydroxymethyl)-2-pyrrolidinone | 62400-75-3 | C5H9NO2 | 详情 | 详情 |
| (VIII) | 22670 | benzyl (E)-3-(5-oxo-2-pyrrolidinyl)-2-propenoate | C14H15NO3 | 详情 | 详情 | |
| (IX) | 22671 | 4-Methoxybenzoyl chloride; p-Methoxybenzoyl chloride; 4-Anisoyl chloride | 100-07-2 | C8H7ClO2 | 详情 | 详情 |
| (X) | 22672 | benzyl (E)-3-[1-(4-methoxybenzoyl)-5-oxo-2-pyrrolidinyl]-2-propenoate | C22H21NO5 | 详情 | 详情 |