methyl (3R)-3-{[(benzyloxy)carbonyl]amino}butanoate -Drug Synthesis Database

【结构式】

【分子编号】58216

【品名】methyl (3R)-3-{[(benzyloxy)carbonyl]amino}butanoate

【CA登记号】

【分子式】C₁₃H₁₇NO₄

【分子量】251.28232

【元素组成】C 62.14% H 6.82% N 5.57% O 25.47%

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：(VI)

Methyl (R)-3-aminobutyrate (I) is protected as the N-Boc derivative (II) using di-tert-butyl dicarbonate. Diastereoselective alkylation of the lithium enolate of (II) with 3-cyanobenzyl bromide (III) yields adduct (IV). Deprotection of (IV) is then effected by treatment with trifluoroacetic acid, to afford amino ester (V). Alternatively, aminobutyrate (I) is protected as the N-(benzyloxycarbonyl) derivative (VI), which is then alkylated with 3-cyanobenzyl bromide (III) to give (VII). Catalytic hydrogenolysis of (VII) in the presence of Pd/C yields the target intermediate (V).

参考文献中间体

合成目标

【1】 Guertin, K.R.; Klein, S.I.; Spada, A.P. (Aventis Pharma SA); Substd. N-[(aminoiminomethyl or aminomethyl)phenyl]propyl amides. EP 0906094; JP 2000502710; US 6080767; WO 9724118 .
【2】 Gong, Y.; Guertin, K.R.; McGarry, D.G.; Pauls, H.W.; Klein, S.I.; Spada, A.P. (Aventis Pharmaceuticals, Inc.); Substd. N-[(aminoiminomethyl or aminomethyl)phenyl]propyl amides. CA 2264556; EP 0931060; WO 9900356 .

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)	38456	methyl (3R)-3-aminobutanoate		C₅H₁₁NO₂	详情	详情
(II)	38457	methyl (3R)-3-[(tert-butoxycarbonyl)amino]butanoate		C₁₀H₁₉NO₄	详情	详情
(III)	13244	alpha-Bromo-m-tolunitrile; 3-(Bromomethyl)benzonitrile	28188-41-2	C₈H₆BrN	详情	详情
(IV)	38458	methyl (2R,3R)-3-[(tert-butoxycarbonyl)amino]-2-(3-cyanobenzyl)butanoate		C₁₈H₂₄N₂O₄	详情	详情
(V)	38459	methyl (2R,3R)-3-amino-2-(3-cyanobenzyl)butanoate		C₁₃H₁₆N₂O₂	详情	详情
(VI)	58216	methyl (3R)-3-{[(benzyloxy)carbonyl]amino}butanoate		C₁₃H₁₇NO₄	详情	详情
(VII)	38460	methyl (2R,3R)-3-[[(benzyloxy)carbonyl]amino]-2-(3-cyanobenzyl)butanoate		C₂₁H₂₂N₂O₄	详情	详情

Extended Information