tert-butyl (2S)-1-[(4-chloro-3-nitrophenyl)sulfonyl]-2-pyrrolidinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】42319

【品名】tert-butyl (2S)-1-[(4-chloro-3-nitrophenyl)sulfonyl]-2-pyrrolidinecarboxylate

【CA登记号】

【分子式】C₁₅H₁₉ClN₂O₆S

【分子量】390.84444

【元素组成】C 46.1% H 4.9% Cl 9.07% N 7.17% O 24.56% S 8.2%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(III)

Condensation of 4-chloro-3-nitrobenzenesulfonyl chloride (VII) with L-proline tert-butyl ester (VIII) yielded sulfonamide (IX). Displacement of the chloro group of (IX) with hydrazine hydrate furnished the aryl hydrazine (X), which was reacted with benzhydryl isothiocyanate (XI) to produce the thiosemicarbazide (XII). After acid cleavage of the tert-butyl ester of (XII), the resulting carboxylic acid (XIII) was activated with isobutyl chloroformate and then coupled with triamine (VI) to furnish the title amide.

参考文献中间体

合成目标

【1】 Ritchie, T.J.; Hallett, A.; Dziadulewicz, E.K.; et al.; 1-(2-Nitrophenyl)thiosemicarbazides: A novel class of potent, orally active non-peptide antagonist for the bradykinin B2 receptor. J Med Chem 2000, 43, 5, 769.

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)	42318	4-chloro-3-nitrobenzenesulfonyl chloride	97-08-5	C₆H₃Cl₂NO₄S	详情	详情
(II)	19832	tert-butyl (2S)-2-pyrrolidinecarboxylate		C₉H₁₇NO₂	详情	详情
(III)	42319	tert-butyl (2S)-1-[(4-chloro-3-nitrophenyl)sulfonyl]-2-pyrrolidinecarboxylate		C₁₅H₁₉ClN₂O₆S	详情	详情
(IV)	42320	tert-butyl (2S)-1-[(4-hydrazino-3-nitrophenyl)sulfonyl]-2-pyrrolidinecarboxylate		C₁₅H₂₂N₄O₆S	详情	详情
(V)	42321	1-[isothiocyanato(phenyl)methyl]benzene; benzhydryl isothiocyanate	3550-21-8	C₁₄H₁₁NS	详情	详情
(VI)	42322	tert-butyl (2S)-1-[(4-[2-[(benzhydrylamino)carbothioyl]hydrazino]-3-nitrophenyl)sulfonyl]-2-pyrrolidinecarboxylate		C₂₉H₃₃N₅O₆S₂	详情	详情
(VII)	42323	(2S)-1-[(4-[2-[(benzhydrylamino)carbothioyl]hydrazino]-3-nitrophenyl)sulfonyl]-2-pyrrolidinecarboxylic acid		C₂₅H₂₅N₅O₆S₂	详情	详情
(VIII)	42317	N-(2-aminoethyl)-N-[2-(dimethylamino)ethyl]-N-methylamine; N(1)-(2-aminoethyl)-N(1),N(2),N(2)-trimethyl-1,2-ethanediamine		C₇H₁₉N₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

Condensation of anthranilic acid (I) with 4-chloro-3-nitrobenzenesulfonyl chloride (II) in the presence of Na2CO3 affords sulfonamide (III). Electrophilic chlorination of (III) employing sulfuryl chloride in hot AcOH leads to (IV). After activation of acid (IV) as the corresponding acid chloride (V), coupling with 4-chloroaniline (VI) furnishes the target anthranilamide.

参考文献中间体

合成目标

【1】 Allanson, N.M.; Thomas, M.G. (PanTherix Ltd.); Bactericidal benzamide derivs.. GB 2365426 .

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)	11661	2-Aminobenzoic acid;Anthranilic acid; o-Aminobenzoic acid	118-92-3	C₇H₇NO₂	详情	详情
(II)	42319	tert-butyl (2S)-1-[(4-chloro-3-nitrophenyl)sulfonyl]-2-pyrrolidinecarboxylate		C₁₅H₁₉ClN₂O₆S	详情	详情
(III)	64106	2-{[(4-chloro-3-nitrophenyl)sulfonyl]amino}benzoic acid		C₁₃H₉ClN₂O₆S	详情	详情
(IV)	64107	5-chloro-2-{[(4-chloro-3-nitrophenyl)sulfonyl]amino}benzoic acid		C₁₃H₈Cl₂N₂O₆S	详情	详情
(V)	64108	5-chloro-2-{[(4-chloro-3-nitrophenyl)sulfonyl]amino}benzoyl chloride		C₁₃H₇Cl₃N₂O₅S	详情	详情
(VI)	12034	4-Chlorophenylamine; 4-Chloroaniline; p-Chloroaniline	106-47-8	C₆H₆ClN	详情	详情

Extended Information