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【结 构 式】

【分子编号】64429

【品名】2-(tricyclo[3.3.1.1~3,7~]dec-1-yloxy)acetyl chloride

【CA登记号】

【 分 子 式 】C12H17ClO2

【 分 子 量 】228.71848

【元素组成】C 63.02% H 7.49% Cl 15.5% O 13.99%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(III)

Saponification of ethyl adamantyloxyacetate (I), followed by treatment of the resultant carboxylic acid (II) with oxalyl chloride gives rise to acid chloride (III). This is then condensed with benzyl (triphenylphosphoranylidene)acetate (IV) to produce the phosphoranylidene keto ester (V). Subsequent oxidative cleavage of phosphorane (V) with oxone under phase transfer conditions leads to diketo ester (VI). Cyclization between diketo ester (VI), cyclohexanecarboxaldehyde (VII) and ammonium acetate in hot AcOH affords imidazole (VIII). The benzyl ester group of (VIII) is removed by catalytic hydrogenolysis, yielding acid (IX), which is further coupled with benzyl 3-aminobenzoate (X) to furnish amide (XI). Finally, benzyl ester hydrogenolysis in the presence of Pd/C provides the target compound (1,2).

1 Gastrin and cholecystokinin receptor ligands. JP 2002529455; US 6479531; WO 0027823 .
2 Kalindjian, S.B.; Mesens, J.L.; Black, J.W.; Hull, R.A.D.; Shankley, N.P.; Andries, L.J. (James Black Foundation Ltd.; Janssen Pharmaceutica NV); Pharmaceutical compsns. comprising proton pump inhibitors and gastrin/cholecystokinin receptor ligands. WO 0185167 .
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) 64427 ethyl 2-(tricyclo[3.3.1.1~3,7~]dec-1-yloxy)acetate C14H22O3 详情 详情
(II) 64428 2-(tricyclo[3.3.1.1~3,7~]dec-1-yloxy)acetic acid C12H18O3 详情 详情
(III) 64429 2-(tricyclo[3.3.1.1~3,7~]dec-1-yloxy)acetyl chloride C12H17ClO2 详情 详情
(IV) 22668 benzyl 2-(triphenylphosphoranylidene)acetate C27H23O2P 详情 详情
(V) 64430 phenylmethyl 3-oxo-4-(tricyclo[3.3.1.1~3,7~]dec-1-yloxy)-2-(triphenyl-lambda~5~-phosphanylidene)butanoate C39H39O4P 详情 详情
(VI) 64449 phenylmethyl 2,3-dioxo-4-(tricyclo[3.3.1.1~3,7~]dec-1-yloxy)butanoate C21H24O5 详情 详情
(VII) 33694 cyclohexanecarbaldehyde 2043-61-0 C7H12O 详情 详情
(VIII) 64450 phenylmethyl 2-cyclohexyl-5-[(tricyclo[3.3.1.1~3,7~]dec-1-yloxy)methyl]-1H-imidazole-4-carboxylate C28H36N2O3 详情 详情
(IX) 64461 2-cyclohexyl-5-[(tricyclo[3.3.1.1~3,7~]dec-1-yloxy)methyl]-1H-imidazole-4-carboxylic acid C21H30N2O3 详情 详情
(X) 64462 phenylmethyl 3-aminobenzoate C14H13NO2 详情 详情
(XI) 64463 phenylmethyl 3-[({2-cyclohexyl-5-[(tricyclo[3.3.1.1~3,7~]dec-1-yloxy)methyl]-1H-imidazol-4-yl}carbonyl)amino]benzoate C35H41N3O4 详情 详情
Extended Information