　 -Drug Synthesis Database

【结构式】

【分子编号】43148

【品名】　

【CA登记号】

【分子式】C₁₄H₁₇NO₈S

【分子量】359.35692

【元素组成】C 46.79% H 4.77% N 3.9% O 35.62% S 8.92%

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：(V)

7-Aminocephalosporanic acid (I) was converted to tert-butyl ester (II) by treatment with isobutylene and sulfuric acid. Subsequent diazotization, followed by reaction with methanol and rhodium catalyst, provided the 7-methoxy derivative (IIIa-b) as a diastereomeric mixture. The desired 7S-isomer was then deprotected with trifluoroacetic acid in anisole, yielding carboxylic acid (IV). Coupling of acid (IV) with 3-iodobenzylamine (VI) via activation as the mixed anhydride (V) with ethyl chloroformate gave rise to amide (VII). The sulfide group of (VII) was finally converted into the title sulfone by oxidation with oxone.

参考文献中间体

合成目标

【1】 Levy, M.A.; Gleason, J.G. (SmithKline Beecham plc); Interleukin converting enzyme and apoptosis. EP 0851760; JP 1999514345; WO 9707805 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(IIIa)	43145	tert-butyl (6R,7R)-3-[(acetoxy)methyl]-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	C₁₅H₂₁NO₆S	详情	详情
(IIIb)	43146	tert-butyl (6R,7S)-3-[(acetoxy)methyl]-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	C₁₅H₂₁NO₆S	详情	详情
(I)	22747	(6R,7R)-3-[(acetoxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid	C₁₀H₁₂N₂O₅S	详情	详情
(II)	32660	tert-butyl (6R,7R)-3-[(acetoxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	C₁₄H₂₀N₂O₅S	详情	详情
(IV)	43147	(6R,7S)-3-[(acetoxy)methyl]-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid	C₁₁H₁₃NO₆S	详情	详情
(V)	43148		C₁₄H₁₇NO₈S	详情	详情
(VI)	20865	3-iodobenzylamine; (3-iodophenyl)methanamine	C₇H₈IN	详情	详情
(VII)	43149	((6R,7S)-2-[[(3-iodobenzyl)amino]carbonyl]-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl)methyl acetate	C₁₈H₁₉IN₂O₅S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

The synthesis of the 125I-labeled compound is shown in Scheme 2. Carboxylic acid (IV) was coupled with 3-(tri-n-butylstannyl)benzylamine (VIII) via the mixed anhydride (V) to produce amide (IX). Subsequent oxidation with oxone afforded the sulfone (X). Finally, iododestannylation of (X) employing Na125I and chloramine-T furnished the radiolabeled compound.

参考文献中间体

合成目标

【1】 Garnes, K.T.; et al.; Preparation of 3-125I-benzyl-(6R,7S9-7-methoxy-3-acetoxymethyl-3-cephem-4-carboxamide-1,1-dioxide. J Label Compd Radiopharm 1999, 42, 1, 77.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(IV)	43147	(6R,7S)-3-[(acetoxy)methyl]-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid	C₁₁H₁₃NO₆S	详情	详情
(V)	43148		C₁₄H₁₇NO₈S	详情	详情
(VIII)	43150	3-(tributylstannyl)benzylamine; [3-(tributylstannyl)phenyl]methanamine	C₁₉H₃₅NSn	详情	详情
(IX)	43151	[(6R,7S)-7-methoxy-8-oxo-2-([[3-(tributylstannyl)benzyl]amino]carbonyl)-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl acetate	C₃₀H₄₆N₂O₅SSn	详情	详情
(X)	43152	[(6R,7S)-7-methoxy-5,5,8-trioxo-2-([[3-(tributylstannyl)benzyl]amino]carbonyl)-5lambda(6)-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl acetate	C₃₀H₄₆N₂O₇SSn	详情	详情

Extended Information