N-benzyl-2-chloro-N-[(1S)-2-hydroxy-1-methylethyl]acetamide -Drug Synthesis Database

【结构式】

【分子编号】55058

【品名】N-benzyl-2-chloro-N-[(1S)-2-hydroxy-1-methylethyl]acetamide

【CA登记号】

【分子式】C₁₂H₁₆ClNO₂

【分子量】241.71728

【元素组成】C 59.63% H 6.67% Cl 14.67% N 5.79% O 13.24%

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：(V)

Condensation of L-alaninol (I) with benzaldehyde produced imine (II), which was further reduced to the N-benzyl amine (III) by means of NaBH4. Subsequent acylation of N-benzyl alaninol (III) with chloroacetyl chloride (IV) provided the chloroacetamide (V). This was subjected to intramolecular cyclization in the presence of NaH to afford morpholinone (VI). Lactam (VI) reduction employing LiAlH4 furnished the substituted morpholine (VII). The N-benzyl group of (VII) was then removed by hydrogenation in the presence of Pd/C, yielding (S)-3-methylmorpholine (VIII).

参考文献中间体

合成目标

【1】 Powers, J.P. (Tularik Inc.); Arylsulfonic acid salts of pyrimidine-based antiviral agents. US 6410726; WO 0151485 .

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)	14341	L-Alaninol; (2S)-2-Amino-1-propanol; L-(+)-Alaninol	2749-11-3	C₃H₉NO	详情	详情
(II)	55056	(2S)-2-{[(E)-phenylmethylidene]amino}-1-propanol		C₁₀H₁₃NO	详情	详情
(III)	55057	(2S)-2-(benzylamino)-1-propanol		C₁₀H₁₅NO	详情	详情
(IV)	11296	2-Chloroacetyl chloride; Chloroacetic chloride	79-04-9	C₂H₂Cl₂O	详情	详情
(V)	55058	N-benzyl-2-chloro-N-[(1S)-2-hydroxy-1-methylethyl]acetamide		C₁₂H₁₆ClNO₂	详情	详情
(VI)	55059	(5S)-4-benzyl-5-methyl-3-morpholinone		C₁₂H₁₅NO₂	详情	详情
(VII)	55060	(3S)-4-benzyl-3-methylmorpholine		C₁₂H₁₇NO	详情	详情
(VIII)	55061	(3S)-3-methylmorpholine		C₅H₁₁NO	详情	详情

Extended Information