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【结 构 式】 
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【分子编号】63514 【品名】11-{[1-[(2,4-dichlorophenyl)methyl]-4-(3-thiophenyl)-3-pyrrolidinyl]methyl}-3,14-dioxa-11-azadispiro[5.1.5.2]pentadecane-15-carboxylic acid 【CA登记号】 |
【 分 子 式 】C29H36Cl2N2O4S 【 分 子 量 】579.58732 【元素组成】C 60.1% H 6.26% Cl 12.23% N 4.83% O 11.04% S 5.53% |
合成路线1
该中间体在本合成路线中的序号：(XVIII)The N-benzyl group of (XIV) is removed by catalytic hydrogenolysis to yield the secondary amine (XV). Subsequent reductive alkylation of amine (XV) with 2,4-dichlorobenzaldehyde (XVI) leads to the dichlorobenzyl amine (XVII). After alkaline hydrolysis of the methyl ester (XVII), the obtained carboxylic acid (XVIII) is converted to the PMB ester (XIX) employing p-methoxybenzyl chloride and Cs2CO3. The diastereomeric mixture of PMB esters (XIX) is then chromatographically separated by means of a chiral column, and the desired isomer is finally deprotected with trifloroacetic acid to yield the target carboxylic acid
| 【1】 Pyrrolidine antagonists of the CCR3 chemokine receptor. 225th ACS Natl Meet (March 23 2003, New Orleans) 2003, Abst MEDI 250. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XIV) | 63509 | methyl 11-{[1-(phenylmethyl)-4-(3-thiophenyl)-3-pyrrolidinyl]methyl}-3,14-dioxa-11-azadispiro[5.1.5.2]pentadecane-15-carboxylate | C30H40N2O4S | 详情 | 详情 | |
| (XV) | 63511 | methyl 11-{[4-(3-thiophenyl)-3-pyrrolidinyl]methyl}-3,14-dioxa-11-azadispiro[5.1.5.2]pentadecane-15-carboxylate | C23H34N2O4S | 详情 | 详情 | |
| (XVI) | 22196 | 2,4-dichlorobenzaldehyde | 874-42-0 | C7H4Cl2O | 详情 | 详情 |
| (XVII) | 63513 | methyl 11-{[1-[(2,4-dichlorophenyl)methyl]-4-(3-thiophenyl)-3-pyrrolidinyl]methyl}-3,14-dioxa-11-azadispiro[5.1.5.2]pentadecane-15-carboxylate | C30H38Cl2N2O4S | 详情 | 详情 | |
| (XVIII) | 63514 | 11-{[1-[(2,4-dichlorophenyl)methyl]-4-(3-thiophenyl)-3-pyrrolidinyl]methyl}-3,14-dioxa-11-azadispiro[5.1.5.2]pentadecane-15-carboxylic acid | C29H36Cl2N2O4S | 详情 | 详情 | |
| (XIX) | 63515 | [4-(methyloxy)phenyl]methyl 11-{[1-[(2,4-dichlorophenyl)methyl]-4-(3-thiophenyl)-3-pyrrolidinyl]methyl}-3,14-dioxa-11-azadispiro[5.1.5.2]pentadecane-15-carboxylate | C37H44Cl2N2O5S | 详情 | 详情 | |
| (XX) | 63510 | [4-(methyloxy)phenyl]methyl 11-{[1-[(2,4-dichlorophenyl)methyl]-4-(3-thiophenyl)-3-pyrrolidinyl]methyl}-3,14-dioxa-11-azadispiro[5.1.5.2]pentadecane-15-carboxylate | C37H44Cl2N2O5S | 详情 | 详情 |