N-(tert-butoxycarbonyl)-3-fluoro-2-methylalanine -Drug Synthesis Database

【结构式】

【分子编号】61666

【品名】N-(tert-butoxycarbonyl)-3-fluoro-2-methylalanine

【CA登记号】

【分子式】C₉H₁₆FNO₄

【分子量】221.2287832

【元素组成】C 48.86% H 7.29% F 8.59% N 6.33% O 28.93%

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：(IV)

The nonradioactive aminoacid is prepared as follows. The Strecker reaction of fluoroacetone (I) with KCN and NH4Cl provides amino nitrile (II). Acid hydrolysis of (II) gives aminoacid (III), which is further protected as the N-Boc derivative (IV) by using di-t-butyl dicarbonate. Treatment of acid (IV) with t-butyl trichloroacetimidate produces the t-butyl ester (V). Subsequent alkylation of (V) with iodomethane and NaH affords the N-methyl derivative (VI). The protecting groups of (VI) are finally removed by acidic hydrolysis to produce the free aminoacid.

参考文献中间体

合成目标

【1】 McConathy, J.; et al.; Radiolabeled amino acids for tumor imaging with PET: Radiosynthesis and biological evaluation of 2-amino-3[18F]fluoro-2-methylpropanoic acid and 3-[18F]fluoro-2-methyl-2-(methylamino)propanoic acid. J Med Chem 2002, 45, 11, 2240.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	61667	tert-butyl 2,2,2-trichloroethanimidoate		C₆H₁₀Cl₃NO	详情	详情
(I)	61762	Fluoroacetone; 2-Propanone, 1-fluoro-; Fluoroacetone; mono-FLUOROACETONE	430-51-3	C₃H₅FO	详情	详情
(II)	61763	tert-butyl (3S)-3-[(acetyloxy)methyl]-6-(benzyloxy)-5-{[(E)-3-methoxy-1-methyl-3-oxo-1-propenyl]amino}-2,3-dihydro-1H-indole-1-carboxylate		C₄H₇FN₂	详情	详情
(III)	61764	3-fluoro-2-methylalanine		C₄H₈FNO₂	详情	详情
(IV)	61666	N-(tert-butoxycarbonyl)-3-fluoro-2-methylalanine		C₉H₁₆FNO₄	详情	详情
(V)	61668	tert-butyl 2-[(tert-butoxycarbonyl)amino]-3-fluoro-2-methylpropanoate		C₁₃H₂₄FNO₄	详情	详情
(VI)	61669	tert-butyl 2-[(tert-butoxycarbonyl)(methyl)amino]-3-fluoro-2-methylpropanoate		C₁₄H₂₆FNO₄	详情	详情

Extended Information