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【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

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).

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.

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