benzyl (1S)-2-amino-1-(4-bromobenzyl)-2-oxoethyl[(2S,3S)-2-hydroxy-3-({(2S)-3-methyl-2-[(2-pyridinylcarbonyl)amino]butanoyl}amino)-4-phenylbutyl]carbamate -Drug Synthesis Database

【结构式】

【分子编号】58401

【品名】benzyl (1S)-2-amino-1-(4-bromobenzyl)-2-oxoethyl[(2S,3S)-2-hydroxy-3-({(2S)-3-methyl-2-[(2-pyridinylcarbonyl)amino]butanoyl}amino)-4-phenylbutyl]carbamate

【CA登记号】

【分子式】C₃₈H₄₂BrN₅O₆

【分子量】744.68558

【元素组成】C 61.29% H 5.68% Br 10.73% N 9.4% O 12.89%

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)

Coupling between epoxide (I) and amine (II) affords amino alcohol (III). The amino group of (III) is then protected with benzyl chloroformate to provide carbamate (IV). Removal of the N-Boc group of (IV) with trifluoroacetic acid yields amine (V), which is subsequently coupled with N-Boc-L-valine (VI) by means of TBTU to furnish amide (VII). After acidic Boc group cleavage in (VII), the resultant amine (VIII) is acylated by picolinic acid (IX) producing amide (X).

参考文献中间体

合成目标

【1】 Noteberg, D.; et al.; New antimalarials: Design and synthesis of protease inhibitors with effect in cultured parasite-infected human erythrocytes. Drugs Fut 2002, 27, Suppl. A.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	23444	tert-butyl (1S)-1-[(2R)oxiranyl]-2-phenylethylcarbamate	C₁₅H₂₁NO₃	详情	详情
(II)	58402	(2S)-2-amino-3-(4-bromophenyl)propanamide	C₉H₁₁BrN₂O	详情	详情
(III)	58396	tert-butyl (1S,2S)-3-{[(1S)-2-amino-1-(4-bromobenzyl)-2-oxoethyl]amino}-1-benzyl-2-hydroxypropylcarbamate	C₂₄H₃₂BrN₃O₄	详情	详情
(IV)	58397	benzyl (1S)-2-amino-1-(4-bromobenzyl)-2-oxoethyl{(2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-4-phenylbutyl}carbamate	C₃₂H₃₈BrN₃O₆	详情	详情
(V)	58398	benzyl (1S)-2-amino-1-(4-bromobenzyl)-2-oxoethyl[(2S,3S)-3-amino-2-hydroxy-4-phenylbutyl]carbamate	C₂₇H₃₀BrN₃O₄	详情	详情
(VI)	19733	(2S)-2-[(tert-butoxycarbonyl)amino]-3-methylbutyric acid	C₁₀H₁₉NO₄	详情	详情
(VII)	58399	benzyl (1S)-2-amino-1-(4-bromobenzyl)-2-oxoethyl[(2S,3S)-3-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-methylbutanoyl}amino)-2-hydroxy-4-phenylbutyl]carbamate	C₃₇H₄₇BrN₄O₇	详情	详情
(VIII)	58400	benzyl (1S)-2-amino-1-(4-bromobenzyl)-2-oxoethyl((2S,3S)-3-{[(2S)-2-amino-3-methylbutanoyl]amino}-2-hydroxy-4-phenylbutyl)carbamate	C₃₂H₃₉BrN₄O₅	详情	详情
(IX)	59950	(chloromethyl)(dimethyl)silyl isopropyl ether; (chloromethyl)(isopropoxy)dimethylsilane	C₆H₁₅ClOSi	详情	详情
(X)	58401	benzyl (1S)-2-amino-1-(4-bromobenzyl)-2-oxoethyl[(2S,3S)-2-hydroxy-3-({(2S)-3-methyl-2-[(2-pyridinylcarbonyl)amino]butanoyl}amino)-4-phenylbutyl]carbamate	C₃₈H₄₂BrN₅O₆	详情	详情

合成路线2

该中间体在本合成路线中的序号：(X)

The N-carbobenzoxy group of (X) is then removed by treatment with triflic acid, yielding (XI). Finally, Suzuki coupling of the aryl bromide (XI) with phenylboronic acid leads to the title biphenyl derivative.

参考文献中间体

合成目标

【1】 Noteberg, D.; et al.; New antimalarials: Design and synthesis of protease inhibitors with effect in cultured parasite-infected human erythrocytes. Drugs Fut 2002, 27, Suppl. A.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(X)	58401	benzyl (1S)-2-amino-1-(4-bromobenzyl)-2-oxoethyl[(2S,3S)-2-hydroxy-3-({(2S)-3-methyl-2-[(2-pyridinylcarbonyl)amino]butanoyl}amino)-4-phenylbutyl]carbamate		C₃₈H₄₂BrN₅O₆	详情	详情
(XI)	58403	N-((1S)-1-{[((1S,2S)-3-{[(1S)-2-amino-1-(4-bromobenzyl)-2-oxoethyl]amino}-1-benzyl-2-hydroxypropyl)amino]carbonyl}-2-methylpropyl)-2-pyridinecarboxamide		C₃₀H₃₆BrN₅O₄	详情	详情

Extended Information