(4S)-4-amino-5-(benzyloxy)-5-oxopentanoic acid -Drug Synthesis Database

【结构式】

【分子编号】42338

【品名】(4S)-4-amino-5-(benzyloxy)-5-oxopentanoic acid

【CA登记号】13030-09-6

【分子式】C₁₂H₁₅NO₄

【分子量】237.25544

【元素组成】C 60.75% H 6.37% N 5.9% O 26.97%

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：(VI)

D-Phenylglycine (I) was converted to ethyl ester (II) by means of ethanol and thionyl chloride. Coupling of N-Fmoc-S-benzylcysteine (III) with amino ester (II) produced the protected dipeptide (IV). The Fmoc group of (IV) was then removed by treatment with piperidine in DMF to give (V). N-Fmoc-glutamic acid alpha-benzyl ester (VII) was prepared by reaction of glutamic acid alpha-benzyl ester (VI) with N-(fluorenylmethoxycarbonyloxy)succinimide. Coupling of protected glutamic acid (VII) with dipeptide (V) furnished tripeptide (VIII). The Fmoc and ester protecting groups of (VIII) were finally cleaved by treatment with NaOH.

参考文献中间体

合成目标

【1】 Lyttle, M.H.; et al.; Isozyme-specific glutathione-S-transferase: Design and synthesis. J Med Chem 1994, 37, 1, 189.
【2】 Kauvar, L.M.; Lyttle, M.H. (Telik, Inc.); Glutathione analogs and paralog panels comprising glutathione mimics. EP 0720620; US 5599903; WO 9508563 .

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)	40170	(2R)-2-amino-2-phenylethanoic acid		C₈H₉NO₂	详情	详情
(II)	42334	ethyl (2R)-2-amino-2-phenylethanoate	17609-48-2	C₁₀H₁₃NO₂	详情	详情
(III)	42335	(2R)-3-(benzylsulfanyl)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]propionic acid		C₂₅H₂₃NO₄S	详情	详情
(IV)	42336	ethyl (2R)-2-[((2R)-3-(benzylsulfanyl)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]propanoyl)amino]-2-phenylethanoate		C₃₅H₃₄N₂O₅S	详情	详情
(V)	42337	ethyl (2R)-2-[[(2R)-2-amino-3-(benzylsulfanyl)propanoyl]amino]-2-phenylethanoate		C₂₀H₂₄N₂O₃S	详情	详情
(VI)	42338	(4S)-4-amino-5-(benzyloxy)-5-oxopentanoic acid	13030-09-6	C₁₂H₁₅NO₄	详情	详情
(VII)	42339	(4S)-5-(benzyloxy)-4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-5-oxopentanoic acid		C₂₇H₂₅NO₆	详情	详情
(VIII)	42340	5-benzyl 13-ethyl (5S,10R,13R)-10-[(benzylsulfanyl)methyl]-1-(9H-fluoren-9-yl)-3,8,11-trioxo-13-phenyl-2-oxa-4,9,12-triazatridecane-5,13-dicarboxylate		C₄₇H₄₇N₃O₈S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

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

Extended Information