tert-butyl (3S)-3-[(2-chloroacetyl)amino]-1-pyrrolidinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】53604

【品名】tert-butyl (3S)-3-[(2-chloroacetyl)amino]-1-pyrrolidinecarboxylate

【CA登记号】n/a

【分子式】C₁₁H₁₉ClN₂O₃

【分子量】262.73624

【元素组成】C 50.29% H 7.29% Cl 13.49% N 10.66% O 18.27%

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)

The pyrrolidine intermediate (VII) has been obtained as follows: The acylation of N-Boc-pyrrolidine-3(R)-amine (I) with chloroacetyl chloride (II) and TEA in dichloromethane gives the acetamide (III), which by treatment with ammonia in methanol/water yields the glycinamide (IV). The reaction of (IV) with protected S-methylisothiourea (V) in methanol affords the protected guanidine (VI). The N-Boc deprotection of (VI) by means of HCl in ethyl acetate/acetonitrile affords the target pyrrolidine intermediate (VII).

参考文献中间体

合成目标

【1】 Kanno, O.; Shibayama, T.; Ohya, S.; Shimoji, Y.; Kuwahara, S.; Ishikawa, K.; Kojima, K.; Kawamoto, I.; R-115685, a novel parenteral carbapenem: Synthesis and structure-activity relationships. 40th Intersci Conf Antimicrob Agents Chemother (Sept 17 2000, Toronto) 2000, Abst F-1229.

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)	53603	tert-butyl (3S)-3-amino-1-pyrrolidinecarboxylate	n/a	C₉H₁₈N₂O₂	详情	详情
(II)	11296	2-Chloroacetyl chloride; Chloroacetic chloride	79-04-9	C₂H₂Cl₂O	详情	详情
(III)	53604	tert-butyl (3S)-3-[(2-chloroacetyl)amino]-1-pyrrolidinecarboxylate	n/a	C₁₁H₁₉ClN₂O₃	详情	详情
(IV)	53605	tert-butyl (3S)-3-[(2-aminoacetyl)amino]-1-pyrrolidinecarboxylate	n/a	C₁₁H₂₁N₃O₃	详情	详情
(V)	53606	1-({[imino(methylsulfanyl)methyl]amino}carbonyl)-4-nitrobenzene	n/a	C₉H₉N₃O₃S	详情	详情
(VI)	53607	tert-butyl (3S)-3-{[2-({imino[(4-nitrobenzoyl)amino]methyl}amino)acetyl]amino}-1-pyrrolidinecarboxylate	n/a	C₁₉H₂₆N₆O₆	详情	详情
(VII)	53608	2-({imino[(4-nitrobenzoyl)amino]methyl}amino)-N-[(3S)pyrrolidinyl]acetamide	n/a	C₁₄H₁₈N₆O₄	详情	详情

Extended Information