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【结 构 式】

【分子编号】43714

【品名】ethyl 2,3-dichloropropanoate

【CA登记号】6628-21-3

【 分 子 式 】C5H8Cl2O2

【 分 子 量 】171.02272

【元素组成】C 35.12% H 4.71% Cl 41.46% O 18.71%

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:(V)

The cyclization of pyridine-3-carbaldehyde (II) with L-cysteine (I) in ethanol gives the thiazolidine derivative (III), which is treated with formic acid, yielding a diastereomeric mixture of formyl derivatives from which the desired (2R,4R)-(IV) is isolated by crystallization. The cyclization of (2R,4R)-(IV) with ethyl 2,3-dichloropropionate (V) by means of TsCl and Et3N affords (2R)-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole-7-carboxylic acid ethyl ester (VI), which is hydrolyzed with NaOH to the corresponding free acid (VII). Finally, this compound is condensed with 3-aminobenzophenone (VIII) by means of SOCl2 to provide the target amide.

1 (Aventis SA); 1H,3H-pyrrolo[1,2-c]thiazole derivs.. EP 0253711; FR 2601015; JP 1988022589 .
2 Rajoharison, H.G. (Aventis Pharma SA); Process for the preparation of dextrorotatory 3-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]-7-thiazolecarboxylic acid. EP 0297987; US 4906757 .
3 Lavé, D.; James, C.; Rajoharison, H.; Bost, P.E.; Cavero, I.; PYRROLO[1,2-c]THIAZOLE DERIVATIVES: POTENT PAF RECEPTOR ANTAGONISTS. Drugs Fut 1989, 14, 9, 891.
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) 14643 L-cysteine; (R)-2-Amino-3-mercaptopropionic acid 52-90-4 C3H7NO2S 详情 详情
(II) 12849 Nicotinaldehyde; 3-Pyridinecarboxaldehyde 500-22-1 C6H5NO 详情 详情
(III) 38634 (4R)-2-(3-pyridinyl)-1,3-thiazolidine-4-carboxylic acid C9H10N2O2S 详情 详情
(IV) 43713 (2R,4R)-3-formyl-2-(3-pyridinyl)-1,3-thiazolidine-4-carboxylic acid C10H10N2O3S 详情 详情
(V) 43714 ethyl 2,3-dichloropropanoate 6628-21-3 C5H8Cl2O2 详情 详情
(VI) 43715 ethyl (3R)-3-(3-pyridinyl)-1H-pyrrolo[1,2-c][1,3]thiazole-7-carboxylate C14H14N2O2S 详情 详情
(VII) 43716 (3R)-3-(3-pyridinyl)-1H-pyrrolo[1,2-c][1,3]thiazole-7-carboxylic acid C12H10N2O2S 详情 详情
(VIII) 39112 3-Aminobenzophenone; (3-aminophenyl)(phenyl)methanone 2835-78-1 C13H11NO 详情 详情
Extended Information