methyl (2S)-2-(dibenzylamino)propanoate -Drug Synthesis Database

【结构式】

【分子编号】47262

【品名】methyl (2S)-2-(dibenzylamino)propanoate

【CA登记号】

【分子式】C₁₈H₂₁NO₂

【分子量】283.37028

【元素组成】C 76.3% H 7.47% N 4.94% O 11.29%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(II)

Alanine methyl ester (I) was protected by N-alkylation with benzyl bromide to afford (II), which was further reduced to amino alcohol (III) using LiAlH4. Swern oxidation of (III) provided aldehyde (IV). Addition of the Grignard reagent obtained from 1-bromopentadecane (A) to aldehyde (IV) produced the anti-aminoalcohol (V). The N-benzyl groups were finally removed by catalytic hydrogenolysis.

参考文献中间体

合成目标

【1】 Cuadros, R.; et al.; The marine compound spisulosine, an inhibitor of cell proliferation, promotes the disassembly of actin stress fibers. Cancer Letters 2000, 152, 1, 23.
【2】 Garcia Gravalos, D.; Warwick, R.A.; Avila, J.; Rinehart, K.L.; Fregeau, N.L.; Faircloth, G.T. (University of Illinois); Spisulosine cpds. having antitumour activity. WO 9952521 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(A)	47265	bromo(tetradecyl)magnesium	C₁₄H₂₉BrMg	详情	详情
(I)	20694	methyl (2S)-2-aminopropanoate	C₄H₉NO₂	详情	详情
(II)	47262	methyl (2S)-2-(dibenzylamino)propanoate	C₁₈H₂₁NO₂	详情	详情
(III)	47263	(2S)-2-(dibenzylamino)-1-propanol	C₁₇H₂₁NO	详情	详情
(IV)	47264	(2S)-2-(dibenzylamino)propanal	C₁₇H₁₉NO	详情	详情
(V)	47266	(2S,3R)-2-(dibenzylamino)-3-octadecanol	C₃₂H₅₁NO	详情	详情

Extended Information