L-(-)-N-alpha-Boc-amino-epsilon-caprolactam; tert-butyl (3S)-2-oxoazepanylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】42810

【品名】L-(-)-N-alpha-Boc-amino-epsilon-caprolactam; tert-butyl (3S)-2-oxoazepanylcarbamate

【CA登记号】76944-95-1

【分子式】C₁₁H₂₀N₂O₃

【分子量】228.29148

【元素组成】C 57.87% H 8.83% N 12.27% O 21.02%

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：(X)

Azepinone (X) was obtained by cyclization of Boc-L-lysine (IX) in the presence of NaHCO3 and BOP reagent. Subsequent alkylation of the lactam nitrogen of (X) with benzyl bromoacetate (XI) afforded (XII). After Boc deprotection of (XII) with trifluoroacetic acid, coupling with Boc-L-alanine (XIII) gave dipeptide (XIV). This was subjected to a further deprotection and coupling sequence with Boc-L-tryptophan (XV) to give tripeptide (XVI), and then with Boc-L-glutamine (XVII), yielding (XVIII). Acid deprotection of the Boc group of (XVIII), followed by coupling with p-hydroxyphenylpropionic acid (XIX) provided the peptide amide (XX).

参考文献中间体

合成目标

【1】 Cristau, M.; et al.; Synthesis and biological evaluation of bombesin constrained analogues. J Med Chem 2000, 43, 12, 2356.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IX)	42809	(2S)-6-amino-2-[(tert-butoxycarbonyl)amino]hexanoic acid		C₁₁H₂₂N₂O₄	详情	详情
(X)	42810	L-(-)-N-alpha-Boc-amino-epsilon-caprolactam; tert-butyl (3S)-2-oxoazepanylcarbamate	76944-95-1	C₁₁H₂₀N₂O₃	详情	详情
(XI)	12869	benzyl 2-bromoacetate	5437-45-6	C₉H₉BrO₂	详情	详情
(XII)	42811	benzyl 2-[(3S)-3-[(tert-butoxycarbonyl)amino]-2-oxoazepanyl]acetate	n/a	C₂₀H₂₈N₂O₅	详情	详情
(XIII)	26450	Boc-L-Alanine;(S)-2-((tert-butoxycarbonyl)amino)propanoic acid;N-Boc-L-alanine; (2S)-2-[(tert-butoxycarbonyl)amino]propionic acid	15761-38-3	C₈H₁₅NO₄	详情	详情
(XIV)	42812	benzyl 2-[(3S)-3-([(2S)-2-[(tert-butoxycarbonyl)amino]propanoyl]amino)-2-oxoazepanyl]acetate		C₂₃H₃₃N₃O₆	详情	详情
(XV)	16114	N-alpha-t-BOC-L-tryptophan; (2S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-3-yl)propionic acid	13139-14-5	C₁₆H₂₀N₂O₄	详情	详情
(XVI)	42813	benzyl 2-[(3S)-3-[((2S)-2-[[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-3-yl)propanoyl]amino]propanoyl)amino]-2-oxoazepanyl]acetate		C₃₄H₄₃N₅O₇	详情	详情
(XVII)	31820	(2S)-5-amino-2-[(tert-butoxycarbonyl)amino]-5-oxopentanoic acid	13726-85-7	C₁₀H₁₈N₂O₅	详情	详情
(XVIII)	42814	benzyl 2-((3S)-3-[[(2S,5S,8S)-8-(3-amino-3-oxopropyl)-5-(1H-indol-3-ylmethyl)-2,12,12-trimethyl-4,7,10-trioxo-11-oxa-3,6,9-triazatridec-1-anoyl]amino]-2-oxoazepanyl)acetate		C₃₉H₅₁N₇O₉	详情	详情
(XIX)	25691	3-(4-hydroxyphenyl)propionic acid	501-97-3	C₉H₁₀O₃	详情	详情
(XX)	42815	benzyl 2-[(3S)-3-[((2S)-2-[[(2S)-2-[((2S)-5-amino-2-[[3-(4-hydroxyphenyl)propanoyl]amino]-5-oxopentanoyl)amino]-3-(1H-indol-3-yl)propanoyl]amino]propanoyl)amino]-2-oxoazepanyl]acetate		C₄₃H₅₁N₇O₉	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

Alkylation of 2-(Boc-amino)caprolactam (I) with 4-(bromomethyl)biphenyl (II) in the presence of KOH and tetrabutylammonium iodide produced the N-(biphenylylmethyl) lactam (III). After Boc group cleavage with trifluoroacetic acid, the resulting amino lactam (IV) was coupled with the tyrosine derivative (V) using BOP to furnish the corresponding amide.

参考文献中间体

合成目标

【1】 Mandine, E.; Baholet, I.; Deprez, P.; et al.; SAR and rational design of Src SH2 binders around a heterocyclic scaffold identification of RU84687, a subnanomolar and Src SH2 selective binder. 16th Int Symp Med Chem (Sept 18 2000, Bologna) 2000, Abst PA-17.

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)	42810	L-(-)-N-alpha-Boc-amino-epsilon-caprolactam; tert-butyl (3S)-2-oxoazepanylcarbamate	76944-95-1	C₁₁H₂₀N₂O₃	详情	详情
(II)	31210	4-(bromomethyl)-1,1'-biphenyl	2567-29-5	C₁₃H₁₁Br	详情	详情
(III)	44317	tert-butyl (3S)-1-([1,1'-biphenyl]-4-ylmethyl)-2-oxoazepanylcarbamate		C₂₄H₃₀N₂O₃	详情	详情
(IV)	44318	(3S)-3-amino-1-([1,1'-biphenyl]-4-ylmethyl)-2-azepanone		C₁₉H₂₂N₂O	详情	详情
(V)	44319	(2S)-2-(acetamido)-3-[3-formyl-4-(phosphonooxy)phenyl]propionic acid		C₁₂H₁₄NO₈P	详情	详情

Extended Information