methyl (2R)-3-(benzyloxy)-2-([2-[(tert-butoxycarbonyl)amino]-2-methylpropanoyl]amino)propanoate -Drug Synthesis Database

【结构式】

【分子编号】28102

【品名】methyl (2R)-3-(benzyloxy)-2-([2-[(tert-butoxycarbonyl)amino]-2-methylpropanoyl]amino)propanoate

【CA登记号】

【分子式】C₂₀H₃₀N₂O₆

【分子量】394.46808

【元素组成】C 60.9% H 7.67% N 7.1% O 24.34%

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：(V)

The intermediate dipeptide (VI) was prepared by two similar ways. Treatment of N-Boc-O-benzyl-D-serine (I) with MeI and K2CO3 produced the methyl ester (II). Subsequent deprotection of the Boc group of (II) with trifluoroacetic acid gave aminoester (III), which was coupled with N-Boc-alpha-methylalanine (IV) using EDC and HOBt yielding (V). Hydrolysis of the resulting dipeptide ester (V) then provided intermediate (VI). In an alternative procedure, N-Boc-alpha-methyl alanine (IV) was activated as the N-hydroxysuccinimidyl ester (VII), which was condensed with O-benzyl-D-serine (VIII) to produce dipeptide (VI).

参考文献中间体

合成目标

【1】 Carpino, P.A.; Lefker, B.A.; Toler, S.M.; et al.; Design, synthesis and biological evaluation of a novel series of pyrazolidone-piperidine growth hormone secretagogues. 216th ACS Natl Meet (Aug. 23-27, Boston) 1998, Abst MEDI 276.
【2】 Carpino, P.A.; Jardine, D.P.A.; Lefker, B.A.; Ragan, J.A. (Pfizer Inc.); Growth-hormone secretagogues. EP 0869968; JP 1999501945; WO 9724369 .

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)	28112	(2R)-3-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]propionic acid		C₁₅H₂₁NO₅	详情	详情
(II)	28100	methyl (2R)-3-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]propanoate		C₁₆H₂₃NO₅	详情	详情
(III)	28101	methyl (2R)-2-amino-3-(benzyloxy)propanoate		C₁₁H₁₅NO₃	详情	详情
(IV)	18471	N-(tert-butoxycarbonyl)-2-methylalanine	30992-29-1	C₉H₁₇NO₄	详情	详情
(V)	28102	methyl (2R)-3-(benzyloxy)-2-([2-[(tert-butoxycarbonyl)amino]-2-methylpropanoyl]amino)propanoate		C₂₀H₃₀N₂O₆	详情	详情
(VI)	28103	(2R)-3-(benzyloxy)-2-([2-[(tert-butoxycarbonyl)amino]-2-methylpropanoyl]amino)propionic acid		C₁₉H₂₈N₂O₆	详情	详情
(VII)	28104	tert-butyl 2-[(2,5-dioxo-1-pyrrolidinyl)oxy]-1,1-dimethyl-2-oxoethylcarbamate		C₁₃H₂₀N₂O₆	详情	详情
(VIII)	28105	(2R)-2-amino-3-(benzyloxy)propionic acid		C₁₀H₁₃NO₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

Treatment of N-Boc-D-serine benzyl ether (I) with methyl iodide and NaHCO3 provided methyl ester (II). Subsequent acid cleavage of the Boc group of (II) gave aminoester (III), which was coupled with N-Boc-alpha-aminoisobutyric acid (IV) to afford dipeptide (V). The methyl ester group of (V) was then hydrolyzed to acid (VI) using LiOH.

参考文献中间体

合成目标

【1】 Growth hormone secretagogues. EP 0933365; WO 9908699 .

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)	28112	(2R)-3-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]propionic acid		C₁₅H₂₁NO₅	详情	详情
(II)	28100	methyl (2R)-3-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]propanoate		C₁₆H₂₃NO₅	详情	详情
(III)	28101	methyl (2R)-2-amino-3-(benzyloxy)propanoate		C₁₁H₁₅NO₃	详情	详情
(IV)	18471	N-(tert-butoxycarbonyl)-2-methylalanine	30992-29-1	C₉H₁₇NO₄	详情	详情
(V)	28102	methyl (2R)-3-(benzyloxy)-2-([2-[(tert-butoxycarbonyl)amino]-2-methylpropanoyl]amino)propanoate		C₂₀H₃₀N₂O₆	详情	详情
(VI)	28103	(2R)-3-(benzyloxy)-2-([2-[(tert-butoxycarbonyl)amino]-2-methylpropanoyl]amino)propionic acid		C₁₉H₂₈N₂O₆	详情	详情

Extended Information