(2R)-2-[(tert-butoxycarbonyl)amino]-3-(tritylsulfanyl)propionic acid -Drug Synthesis Database

【结构式】

【分子编号】38791

【品名】(2R)-2-[(tert-butoxycarbonyl)amino]-3-(tritylsulfanyl)propionic acid

【CA登记号】21947-98-8

【分子式】C₂₇H₂₉NO₄S

【分子量】463.5976

【元素组成】C 69.95% H 6.31% N 3.02% O 13.8% S 6.92%

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：(XI)

Protected L-cysteine (XI) was converted to aldehyde (XIII) via formation of the corresponding N-methoxy amide (XII) and further reduction with LiAlH4. Reductive condensation of amine (X) with aldehyde (XIII) in the presence of NaBH4CN furnished (XIV). The Boc group of (XIV) was finally deprotected by treatment with trifluoroacetic acid in the presence of triethylsilane.

参考文献中间体

合成目标

【1】 Dong, Z.X.; Kim, S.H. (Biomeasure Inc.); Inhibitors of prenyl transferases. WO 9800409 .

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)	38790	methyl (2S)-2-[([(4R)-3-[(2S,3S)-2-amino-3-methylpentyl]-5,5-dimethyl-1,3-thiazolidin-4-yl]carbonyl)amino]-4-(methylsulfanyl)butanoate		C₁₈H₃₅N₃O₃S₂	详情	详情
(XI)	38791	(2R)-2-[(tert-butoxycarbonyl)amino]-3-(tritylsulfanyl)propionic acid	21947-98-8	C₂₇H₂₉NO₄S	详情	详情
(XII)	38792	tert-butyl (1R)-2-[methoxy(methyl)amino]-2-oxo-1-[(tritylsulfanyl)methyl]ethylcarbamate		C₂₉H₃₄N₂O₄S	详情	详情
(XIII)	17953	tert-butyl (1R)-1-formyl-2-(tritylsulfanyl)ethylcarbamate		C₂₇H₂₉NO₃S	详情	详情
(XIV)	38793	methyl (2S)-2-([[(4R)-3-((2S,3S)-2-[[(2R)-2-[(tert-butoxycarbonyl)amino]-3-(tritylsulfanyl)propyl]amino]-3-methylpentyl)-5,5-dimethyl-1,3-thiazolidin-4-yl]carbonyl]amino)-4-(methylsulfanyl)butanoate		C₄₅H₆₄N₄O₅S₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

Acylation of 2-amino-5-nitrobenzophenone (I) with phenylacetic acid chloride (II) in refluxing toluene yields derivative (III), whose nitro group is reduced by means of SnCl2 in refluxing EtOAc to afford amine (IV). Coupling of (IV) with protected cysteine (V) by means of isobutyl chloroformate and N-methylmorpholine (NMM) in DMF provides protected derivative (VI), which is finally treated with TFA and Et3SiH in CH2Cl2 to furnish the target compound.

参考文献中间体

合成目标

【1】 Schlitzer, M.; et al.; Different amino acid replacement in CAAX-tetrapeptide based peptidomimetic farnesyltransferase inhibitors. Archiv der Pharmazie 1999, 332, 4, 124.
【2】 Grabley, S.; Thiericke, R.; Sattler, I. (Hans Knoll Institute for Natural Product Research); Cysteine amides as farnesyl transferase inhibitors. DE 19851714; WO 0027803 .

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)	43770	(2-amino-5-nitrophenyl)(phenyl)methanone	1775-95-7	C₁₃H₁₀N₂O₃	详情	详情
(II)	25890	2-phenylacetyl chloride；Phenylacetyl chloride;Phenacetyl chloride;Benzeneacetyl chloride	103-80-0	C₈H₇ClO	详情	详情
(III)	43371	4-(2,4-dimethoxy-6-methylphenyl)-3-methyl-1H-pyrazol-5-ylamine; 4-(2,4-dimethoxy-6-methylphenyl)-3-methyl-1H-pyrazol-5-amine		C₁₃H₁₇N₃O₂	详情	详情
(IV)	43772	N-(4-amino-2-benzoylphenyl)-2-phenylacetamide		C₂₁H₁₈N₂O₂	详情	详情
(V)	38791	(2R)-2-[(tert-butoxycarbonyl)amino]-3-(tritylsulfanyl)propionic acid	21947-98-8	C₂₇H₂₉NO₄S	详情	详情
(VI)	43773	tert-butyl (1R)-2-[3-benzoyl-4-[(2-phenylacetyl)amino]anilino]-2-oxo-1-[(tritylsulfanyl)methyl]ethylcarbamate		C₄₈H₄₅N₃O₅S	详情	详情

Extended Information