allyl (2S,4S)-4-(acetylsulfanyl)-2-(chlorocarbonyl)-1-pyrrolidinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】39651

【品名】allyl (2S,4S)-4-(acetylsulfanyl)-2-(chlorocarbonyl)-1-pyrrolidinecarboxylate

【CA登记号】

【分子式】C₁₁H₁₄ClNO₄S

【分子量】291.7552

【元素组成】C 45.28% H 4.84% Cl 12.15% N 4.8% O 21.94% S 10.99%

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：(X)

The sulfanylpyrrolidine (V) can be obtained as follows: Esterification of 3-nitrobenzoic acid (VII) with allyl bromide and K2CO3 in DMF gives the corresponding allyl ester (VIII), which is reduced with SnCl2 in refluxing ethyl acetate to yield the 3-aminobenzoate (IX). The condensation of (IX) with the pyrrolidinecarbonyl chloride (X), obtained from the corresponding carboxylic acid (XI) and oxalyl chloride, by means of NMM in dichloro-methane affords the expected amide (XII), which is finally deacetylated with NaOH in allyl alcohol.

参考文献中间体

合成目标

【1】 Betts, M.J.; Davies, G.M.; Swain, M.L. (AstraZeneca plc); Carbapenems containing a carboxy substd. phenyl group, processes for their preparation, intermediates and use as antibiotics. EP 0579826; JP 1994506704; US 5478820; US 5652233; US 5856321; WO 9315078 .
【2】 Leeson, P.A.; Rabasseda, X.; Castañer, J.; Sorbera, L.A.; MK-0826. Drugs Fut 2000, 25, 8, 795.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(V)	39646	allyl (2S,4S)-2-([3-[(allyloxy)carbonyl]anilino]carbonyl)-4-sulfanyl-1-pyrrolidinecarboxylate		C₁₉H₂₂N₂O₅S	详情	详情
(VII)	39648	1-Carboxy-3-Nitrobenzene; m-Nitrobenzoic acid; 3-Nitrobenzoic acid; 3-Nitrodracylic acid	121-92-6	C₇H₅NO₄	详情	详情
(VIII)	39649	allyl 3-nitrobenzoate		C₁₀H₉NO₄	详情	详情
(IX)	39650	allyl 3-aminobenzoate		C₁₀H₁₁NO₂	详情	详情
(X)	39651	allyl (2S,4S)-4-(acetylsulfanyl)-2-(chlorocarbonyl)-1-pyrrolidinecarboxylate		C₁₁H₁₄ClNO₄S	详情	详情
(XI)	39652	(2S,4S)-4-(acetylsulfanyl)-1-[(allyloxy)carbonyl]-2-pyrrolidinecarboxylic acid		C₁₁H₁₅NO₅S	详情	详情
(XII)	39653	allyl (2S,4S)-4-(acetylsulfanyl)-2-([3-[(allyloxy)carbonyl]anilino]carbonyl)-1-pyrrolidinecarboxylate		C₂₁H₂₄N₂O₆S	详情	详情

Extended Information