benzyl (2S)-5-[(benzoyloxy)(methyl)amino]-2-[((2S)-2,6-bis{[2,3-bis(acetyloxy)benzoyl]amino}hexanoyl)amino]-5-oxopentanoate -Drug Synthesis Database

【结构式】

【分子编号】58520

【品名】benzyl (2S)-5-[(benzoyloxy)(methyl)amino]-2-[((2S)-2,6-bis{[2,3-bis(acetyloxy)benzoyl]amino}hexanoyl)amino]-5-oxopentanoate

【CA登记号】

【分子式】C₄₈H₅₀N₄O₁₆

【分子量】938.94236

【元素组成】C 61.4% H 5.37% N 5.97% O 27.26%

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：(VII)

Acylation of L-lysine (I) with 2,3-diacetoxybenzoyl chloride (II) provides the dibenzoyl lysine derivative (III). After activation of (III) as the corresponding mixed anhydride with isobutyl chloroformate, condensation with alpha-benzyl L-glutamate (IV) yields the dipeptide compound (V). This is further coupled with N-(benzoyloxy) methylamine (VI), via the mixed anhydride with isobutyl chloroformate, to furnish hydroxamate (VII).

参考文献中间体

合成目标

【1】 Wittmann, S.; et al.; New synthetic siderophores and their beta-lactam conjugates based on diamino acids and dipeptides. Bioorg Med Chem 2002, 10, 6, 1659.

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)	20927	L-lysine	56-87-1	C₆H₁₄N₂O₂	详情	详情
(II)	58506	2-(acetyloxy)-3-(chlorocarbonyl)phenyl acetate		C₁₁H₉ClO₅	详情	详情
(III)	58517	(2S)-2,6-bis{[2,3-bis(acetyloxy)benzoyl]amino}hexanoic acid		C₂₈H₃₀N₂O₁₂	详情	详情
(IV)	42338	(4S)-4-amino-5-(benzyloxy)-5-oxopentanoic acid	13030-09-6	C₁₂H₁₅NO₄	详情	详情
(V)	58518	(4S)-5-(benzyloxy)-4-[((2S)-2,6-bis{[2,3-bis(acetyloxy)benzoyl]amino}hexanoyl)amino]-5-oxopentanoic acid		C₄₀H₄₃N₃O₁₅	详情	详情
(VI)	58519	1-{[(methylamino)oxy]carbonyl}benzene		C₈H₉NO₂	详情	详情
(VII)	58520	benzyl (2S)-5-[(benzoyloxy)(methyl)amino]-2-[((2S)-2,6-bis{[2,3-bis(acetyloxy)benzoyl]amino}hexanoyl)amino]-5-oxopentanoate		C₄₈H₅₀N₄O₁₆	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VII)

Catalytic hydrogenolysis of benzyl ester (VII) affords carboxylic acid (VIII) (1). Then, coupling of acid (VIII) with ampicillin (IX) using isobutyl chloroformate provides the target adduct, which is finally converted to the title sodium salt upon treatment with sodium 2-ethylhexanoate in EtOAc.

参考文献中间体

合成目标

【1】 Wittmann, S.; et al.; New synthetic siderophores and their beta-lactam conjugates based on diamino acids and dipeptides. Bioorg Med Chem 2002, 10, 6, 1659.
【2】 Heinisch, L.; Mollmann, U.; Wittmann, S. (Grunenthal GmbH); Siderophore antibiotic conjugates with tetra- or hexadentate iron chelators on the basis of amino acids or peptides, method for producing them and the use thereof. DE 10111163; WO 0270017 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VII)	58520	benzyl (2S)-5-[(benzoyloxy)(methyl)amino]-2-[((2S)-2,6-bis{[2,3-bis(acetyloxy)benzoyl]amino}hexanoyl)amino]-5-oxopentanoate		C₄₈H₅₀N₄O₁₆	详情	详情
(VIII)	58521	(2S)-5-[(benzoyloxy)(methyl)amino]-2-[((2S)-2,6-bis{[2,3-bis(acetyloxy)benzoyl]amino}hexanoyl)amino]-5-oxopentanoic acid		C₄₁H₄₄N₄O₁₆	详情	详情
(IX)	31107	(2S,5R,6R)-6-[[(2R)-2-amino-2-phenylethanoyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	69-53-4	C₁₆H₁₉N₃O₄S	详情	详情

Extended Information