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【结 构 式】

【分子编号】39523

【品名】N-[(2S)-3-anilino-3-oxo-2-(propionylamino)propyl]-N-(benzyloxy)benzamide

【CA登记号】

【 分 子 式 】C26H27N3O4

【 分 子 量 】445.5182

【元素组成】C 70.1% H 6.11% N 9.43% O 14.36%

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:(L)-(VI)

Ethyl 2,3-dibromopropionate (I) is condensed with N-tosyl-O-benzylhydroxylamine (A) by means of NaOEt in ethanol to give after a treatment with ammonia, propionic acid (II), which is detosylated by treatment with phenol and 36% HBr- yielding D,L-2-amino-3-(benzyloxyamino)propionic acid (III). The benzoylation of (III) with N-benzoyloxysuccinimide (B) by means of Triton B - in methanol affords D,L-2-benzoylamino-3-benzyloxyaminopropionic acid (IV), which is resolved into its optical isomers by treatment with aniline (C) and papain in 0.5M NaOH - 0.5M citric acid and L-cysteine hydrochloride; L-2-benzoylamino-3-benzyloxyaminopropionanilide (L)-(V) was isolated. The benzoylation of (L)-(V) with benzoyl chloride (D) in pyridine affords L-2-benzoylamino-3-(N-benzoyl-N-benzyloxyamino)propionanilide (L)-(VI), which is debenzylated by hydrogenation with H2 over Pd/C in methanol giving L-2-benzoylamino-3-(N-benzoyl-N-hydroxyamino)propionanilide (L)-(VII). The protecting groups of (L)-(VII) are eliminated by treatment with 6M HCl at 90-5 C yielding L-2-amino-3-hydroxyaminopropionic acid (L)-(VIII), which is finally nitrosated with NaNO2 and HCl.

1 Serradell, M.N.; Castañer, J.; Cabanillas, F.; Blancafort, P.; Alanosine. Drugs Fut 1979, 4, 7, 469.
2 Yoshikazu, I.; et al.; Synthesis of alanosine. Bull Chem Soc Jpn 1973, 46, 1847-50.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(D) 10463 Benzoyl chloride 98-88-4 C7H5ClO 详情 详情
(A) 39517 N-(benzyloxy)-4-methylbenzenesulfonamide C14H15NO3S 详情 详情
(B) 39520 1-(benzoyloxy)-2,5-pyrrolidinedione C11H9NO4 详情 详情
(L)-(V) 39522 N-((1S)-2-anilino-1-[[(benzyloxy)amino]methyl]-2-oxoethyl)benzamide C23H23N3O3 详情 详情
(L)-(VI) 39523 N-[(2S)-3-anilino-3-oxo-2-(propionylamino)propyl]-N-(benzyloxy)benzamide C26H27N3O4 详情 详情
(L)-(VII) 39524 N-((1S)-2-anilino-1-[[benzoyl(hydroxy)amino]methyl]-2-oxoethyl)benzamide C23H21N3O4 详情 详情
(L)-(VIII) 39525 (2S)-2-amino-3-(hydroxyamino)propionic acid C3H8N2O3 详情 详情
(I) 18341 ethyl 2,3-dibromopropanoate 3674-13-3 C5H8Br2O2 详情 详情
(II) 39518 3-[(benzyloxy)[(4-methylphenyl)sulfonyl]amino]alanine C17H20N2O5S 详情 详情
(III) 39519 3-[(benzyloxy)amino]alanine C10H14N2O3 详情 详情
(IV) 39521 N-benzoyl-3-[(benzyloxy)amino]alanine C17H18N2O4 详情 详情
(C) 12294 Aniline; Phenylamine 62-53-3 C6H7N 详情 详情
Extended Information