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【结 构 式】 
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【分子编号】61243 【品名】 【CA登记号】 |
【 分 子 式 】C18H31NO5 【 分 子 量 】341.44788 【元素组成】C 63.32% H 9.15% N 4.1% O 23.43% |
合成路线1
该中间体在本合成路线中的序号：(VI)The title compound has been prepared by solid phase synthesis. Attachment of (R)-2-butylsuccinic acid 1-fluorenylmethyl ester (I) to ArgoGel resin under Mitsunobu conditions affords the succinate-bound resin (II). Subsequent deprotection with piperidine in DMF leads to the acid-resin (III), which is further activated as the pentafluorophenyl ester (IV) upon treatment with pentafluorophenyl trifluoroacetate. Coupling of active ester (IV) with L-proline tert-butyl ester (V) furnishes amide (VI). Finally, cleavage of the resin by means of hydroxylamine in aqueous dioxane provides the target hydroxamic acid.
| 【1】 Jacobs, J.W.; Yuan, Z.; Ni, Z.-J.; Jain, R.; Patel, D.; Novel succinate cpds., compsns. and methods of use and preparation. US 2002115863 . |
| 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) | 61240 | (3R)-3-[(9H-fluoren-9-ylmethoxy)carbonyl]heptanoic acid | C22H24O4 | 详情 | 详情 | |
| (II) | 61240 | (3R)-3-[(9H-fluoren-9-ylmethoxy)carbonyl]heptanoic acid | C22H24O4 | 详情 | 详情 | |
| (III) | 61241 | (2R)-2-butylbutanedioic acid | C8H14O4 | 详情 | 详情 | |
| (IV) | 61242 | (3R)-3-[(2,3,4,5,6-pentafluorophenoxy)carbonyl]heptanoic acid | C14H13F5O4 | 详情 | 详情 | |
| (V) | 19832 | tert-butyl (2S)-2-pyrrolidinecarboxylate | C9H17NO2 | 详情 | 详情 | |
| (VI) | 61243 | C18H31NO5 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(III)In an alternative procedure, (R)-2-butylsuccinic acid 4-methyl ester (I) is coupled to L-proline tert-butyl ester (II) to afford amide (III). Then, displacement of the methyl ester group with hydroxylamine gives rise to the desired hydroxamic acid.
| 【1】 Jacobs, J.W.; Yuan, Z.; Ni, Z.-J.; Jain, R.; Patel, D.; Novel succinate cpds., compsns. and methods of use and preparation. US 2002115863 . |