147011-39-0Relevant articles and documents
A 5-benzyl -7 (S)-tert-butoxycarbonylamino-5-azaspiro [2,4] heptane preparation method of
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Paragraph 0040-0042, (2017/01/23)
The invention discloses a preparation method for 5-benzyl-7(S)-t-butyloxycarborylamino-5-aza-spiro[2,4]heptane. The method comprises the following steps: reacting benzoylamide acetoacetate as a raw material with 1,2-dichloroethane to obtain 3-cyclopropyl benzoylamide acetoacetate, brominating 3-cyclopropyl benzoylamide acetoacetate by NBS (n-bromosuccinimide) to obtain 1-bromo-3-cyclopropyl benzoylamide acetoacetate, cyclizing under alkaline conditions to obtain 5-benzyl-5-aza-spiro[2,4]heptane-4,7-diketone, further reacting with hydroxylamine hydrochloride to form an oxime compound-4-oxo-5-benzyl-7-oximido-5-aza-spiro[2,4]heptane, reducing by NaBH4 and boron trifluoride diethyl etherate to obtain 5-benzyl-7-amino-5-aza-spiro[2,4]heptane, performing chiral resolution by a resolving agent-L-camphorsulfonic acid to obtain 5-benzyl-7(S)-amino-5-aza-spiro[2,4]heptane, and reacting with di-tert-butyl dicarbonate ester to obtain 5-benzyl-7(S)-t-butyloxycarborylamino-5-aza-spiro[2,4]heptane. According to the method, an intermediate body-carbonyl does not need protection, raw materials are easy to get, a process route is simple, and the method is suitable for industrial production.
Synthesis and In-Vitro Activity of Novel 1β-Methylcarbapenems Having Spiro[2,4]heptane Moieties
Park, Hyeong Beom,Jo, Nam Hyun,Hong, Joon Hee,Chei, Jung Hoon,Cho, Jung-Hyuck,Yoo, Kyung Ho,Oh, Chang-Hyun
, p. 530 - 537 (2008/12/21)
The synthesis of a new series of 1β-methylcarbapenems having spiro[2,4]heptane moieties is described. Their in-vitro antibacterial activities against both gram-positive and gram-negative bacteria were tested and the effect of substituents on the pyrrolidine ring was investigated. Most compounds were shown to be more active than the compared meropenem and imipenem against Escherichia coli. One particular compound, IIIb, having hydroxy a moiety showed the most potent antibacterial activity.