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【结 构 式】 
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【分子编号】45628 【品名】Ethyl (Z)-3-amino-2-butenoate; 3-amino-2-butenoic acid ethyl ester; Ethyl 3-aminocrotonate; 3-Aminocrotonic acid ethyl ester 【CA登记号】626-34-6 |
【 分 子 式 】C6H11NO2 【 分 子 量 】129.15888 【元素组成】C 55.8% H 8.58% N 10.84% O 24.77% |
合成路线1
该中间体在本合成路线中的序号：(II)Condensation of 2-formylcycloheptanone (I) with ethyl 3-aminocrotonate (II) provides ethyl carboxylate (III), which is then converted into carbonylguanidine (VI) by reaction with free guanidine (V) (obtained from guanidine hydrochloride (IV) by treatment with Na/MeOH) in refluxing isopropanol. Alternatively, carbonylguanidine (VI) can also be obtained by saponification of ethyl ester (III) with refluxing NaOH to yield carboxylic acid (VII), which is then activated with oxalyl chloride (A) in CH2Cl2 or with CDI in THF to allow condensation with guanidine (V) in THF. Finally, the corresponding maleate can be obtained by reaction of carbonylguanidine (VI) with maleic acid (VIII) in MeOH.
| 【1】 Kogi, K.; Takahashi, A.; Gengyou, K.; Aihara, K.; Yoneyama, F.; Sasamori, J.; Yoneyama, S.; Satoh, T.; Yamada, S.; Kimura, T. (Toa Eiyo Ltd.); Cycloalka[b]pyridine-3-carbonylguanidine derivs., process for producing the same, and drugs containing the same. EP 0972767; WO 9839300 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IV),(V) | 14790 | Guanidine | 113-00-8 | CH5N3 | 详情 | 详情 |
| (A) | 29841 | Oxalyl chloride; 2-Chloro-2-oxoacetyl chloride | 79-37-8 | C2Cl2O2 | 详情 | 详情 |
| (I) | 45624 | 2-oxocycloheptanecarbaldehyde | 641-70-3 | C8H12O2 | 详情 | 详情 |
| (II) | 45628 | Ethyl (Z)-3-amino-2-butenoate; 3-amino-2-butenoic acid ethyl ester; Ethyl 3-aminocrotonate; 3-Aminocrotonic acid ethyl ester | 626-34-6 | C6H11NO2 | 详情 | 详情 |
| (III) | 45625 | ethyl 2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate | C14H19NO2 | 详情 | 详情 | |
| (VI) | 45626 | N-[(2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-3-yl)carbonyl]guanidine | C13H18N4O | 详情 | 详情 | |
| (VII) | 45627 | 2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylic acid | C12H15NO2 | 详情 | 详情 | |
| (VIII) | 37495 | Maleic acid; (Z)-2-Butenedioic acid | 110-16-7 | C4H4O4 | 详情 | 详情 |